Hydrochloric Acid → 5-Acetyl-1H-indole-2-carboxylic acid

HRID 1665796Notes

Reaction equation

HRID 1665796 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15](=[O:17])[CH3:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.C([O:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=2)=[O:22])C.[OH-].[K+].Cl>C(O)C>[C:15]([C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:4]([OH:5])=[O:3])(=[O:17])[CH3:16].[C:32]([C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([C:21]([OH:22])=[O:20])=[CH:31]2)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4162576HCID 4162576, compoundHCID 11770291HCID 11770291, compound

Product 2

HCID 137058095-Acetyl-1H-indole-2-carboxylic acidHCID 150904433-Acetyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Saponification of 2b and 3b with 10% KOH in ethanol at 60° C. for 1 h followed by acidification with 1M HCl provided 3-acetyl-1H-indole-2-carboxylic acid 4b and 5-acetyl-1H-indole-2-carboxylic acid 5b in 95% and 93% yield respectively. The crude acids were used directly without further purification.

Sources & evidence

ORD record
ord-810ac86246c9425ebff1b029c8ab0c95
Source dataset
uspto-grants-2011_10
Patent number
US08039623B2

Reaction notes

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