Acetic Anhydride → Thiazolo[4,5-c]pyridine-2-carbaldehyde

HRID 615805Notes

Reaction equation

HRID 615805 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.C(OC(=O)C)(=[O:13])C>CC(O)=O>[CH:1]([C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1)=[O:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 6407212-Methyl-[1,3]thiazolo[4,5-c]pyridine

Product 1

HCID 15593552Thiazolo[4,5-c]pyridine-2-carbaldehydeYield 35.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-methylthiazolo[4,5-c]pyridine [prepared according to the procedure of T. Takahashi et al., Pharm. Bull. (Japan) 2, 196 (1954)] (635 mg, 4.2 mmoles), 2.55 g of SeO2, 10 ml of CH3COOH and 10 ml of acetic anhydride was heated at 90 100° C. for 2.5 hours, and the reaction mixture then was filtered to remove insolubles. The filtrate was evaporated in vacuo, and purified by a column of SiO2 (50 ml) to give 248 mg (35.5%) of the title compound. Mp. 96.5°~98° C.

Workup

  1. customprepared
  2. filtrationthe reaction mixture then was filtered
  3. customto remove insolubles
  4. customThe filtrate was evaporated in vacuo
  5. custompurified by a column of SiO2 (50 ml)

Sources & evidence

ORD record
ord-f7302cb7e27d494285267dc5dac02766
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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