Synthesis of substituted salicylaldehyde derivatives

Patent metadata

Field	Value
Publication number	US-10442816-B2
Application number	US-201816024955-A
Country	US
Kind code	B2
Filing date	Jul 2, 2018
Priority date	Sep 22, 2010
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

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 D2-D8, D10, or D13:

wherein
Z is nitrogen or phosphorus, wherein the formal charge on Z satisfies valency requirements;
X is halogen; C 6 -C 20 aryloxy; C 1 -C 20 carboxy; C 1 -C 20 alkoxy; C 1 -C 20 alkylsulfonato; or C 1 -C 20 amido;
R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 and R 25 are each independently hydrogen; C 1 -C 20 alkyl; C 2 -C 20 alkenyl; C 7 -C 20 alkylaryl; or C 7 -C 20 arylalkyl; or two of R 11 , R 12 and R 13 , or two of R 21 , R 22 , R 23 , R 24 and R 25 being optionally fused together to form a bridged structure;
R 31 , R 32 and R 33 are each independently hydrogen; C 1 -C 20 alkyl; C 2 -C 20 alkenyl; C 7 -C 20 alkylaryl; or two of R 31 , R 32 and R 33 being optionally fused together to form a bridged structure;
R 62 is hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
n is from 1 to 20;
X′ is oxygen, sulfur or N—R; and
R is hydrogen; C 1 -C 20 alkyl; C 2 -C 20 alkenyl; C 7 -C 20 alkylaryl; or C 7 -C 20 arylalkyl.

2. The compound of claim 1 , wherein the compound is of formula D5.

3. The compound of claim 1 , wherein the compound is of formula D8.

4. The compound of any one of claim 1 , wherein each Z is nitrogen.

5. The compound of any one of claim 1 , wherein R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 and R 25 are each independently C 1 -C 20 alkyl.

6. The compound of any one of claim 1 , wherein R 62 is hydrogen.

7. The compound of any one of claim 1 , wherein R 62 is methyl, ethyl, n-propyl, isopropyl or tert-butyl.

8. The compound of claim 7 , wherein R 62 is methyl.

9. The compound of claim 7 , wherein R 62 is tert-butyl.

10. The compound of claim 1 , wherein the compound is any one of formulae D9 or D11 through D13:

11. The compound of claim 10 , wherein the compound is of formula D11.

12. The compound of claim 10 , wherein the compound is of formula D12.

13. The compound of claim 10 , wherein the compound is of formula D13.

14. The compound of any one of claim 10 , wherein R 62 is hydrogen.

15. The compound of any one of claim 10 , wherein R 62 is methyl, ethyl, n-propyl, isopropyl or tert-butyl.

16. The compound of claim 15 , wherein R 62 is methyl.

17. The compound of claim 15 , wherein R 62 is tert-butyl.

Assignees

• Saudi Aramco Tech Co

Inventors

• Farmer Jay J
• Job Gabriel E

Classifications

• C07D493/08 Primary

  Bridged systems · CPC title

• C07C221/00

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

• 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