Synthesis of substituted salicylaldehyde derivatives

Patent metadata

Field	Value
Publication number	US-9371334-B2
Application number	US-201414496514-A
Country	US
Kind code	B2
Filing date	Sep 25, 2014
Priority date	Sep 22, 2010
Publication date	Jun 21, 2016
Grant date	Jun 21, 2016

Abstract

Among other things, the present invention encompasses methods of synthesizing salicylaldehyde derivatives comprising the steps of: a) providing salicylaldehyde or a derivative thereof, b) forming an anhydro dimer of the provided salicylaldehyde compound, c) performing one or more chemical transformations on the anhydro dimer and d) hydrolyzing the anhydro dimer to provide a salicylaldehyde derivative different from that provided in step (a).

First claim

What is claimed is:

1. A compound of any one of formulae D14 to D18:

wherein,
R 26 is selected from the group consisting of: hydrogen, halogen, optionally substituted C 1-20 aliphatic, and optionally substituted aryl;
R a and R b are, independently at each occurrence, selected from the group consisting of hydrogen, halogen, and optionally substituted C 1-4 aliphatic;
Q′ is selected from the group consisting of: halogen, hydroxyl, sulfonate ester, a neutral or cationic nitrogen-containing functional group, and a neutral or cationic phosphorous-containing functional group; and
m is from 1 to 10.

2. The compound of claim 1 , wherein Q′ is selected from the group consisting of: bromine, chlorine, iodine, —OH, —OSO 2 R, —N(R) 2 , —N(R) 3 + , —P(R) 3 + , substituted guanidine, guanidinium, and amidine; wherein R is hydrogen; C 1 -C 20 alkyl; C 1 -C 20 alkyl having one or more functional moieties selected from the group consisting of halogen, nitrogen, oxygen, silicon, sulfur, and phosphorus; C 2 -C 20 alkenyl; C 2 -C 20 alkenyl having one or more functional moieties selected from the group consisting of halogen, nitrogen, oxygen, silicon, sulfur, and phosphorus; C 7 -C 20 alkylaryl; C 7 -C 20 alkylaryl having one or more functional moieties selected from the group consisting of halogen, nitrogen, oxygen, silicon, sulfur, and phosphorus; C 7 -C 20 arylalkyl; and C 7 -C 20 arylalkyl having one or more functional moieties selected from the group consisting of halogen, nitrogen, oxygen, silicon, sulfur, and phosphorus.

3. The compound of claim 2 , wherein Q′ is —OH.

4. The compound of claim 2 , wherein Q′ is bromine.

5. The compound of claim 1 , wherein Q′ is a guanidine.

6. The compound of claim 5 , wherein Q′ is 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD).

7. The compound of claim 2 , wherein Q′ is 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene ([N-methyl TBD] + ).

8. The compound of claim 2 , wherein Q′ is trialkylammonium.

9. The compound of claim 1 , wherein R 26 is selected from the group consisting of: —H, halogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl.

10. The compound of claim 9 , wherein R 26 is t-butyl.

11. The compound of claim 1 , wherein m is an integer between 1 and 6.

12. The compound of claim 9 , wherein Q′ is TBD.

13. The compound of claim 9 , wherein Q′ is [N-methyl TBD] + .

Assignees

• Novomer Inc

Inventors

• Farmer Jay J
• Job Gabriel E

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C07D493/08 Primary

  Bridged systems · CPC title

• C07D221/00

  Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 · CPC title

• C07C221/00

  Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title