Water → 4-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid

HRID 1860875

Reaction equation

C([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[C:9]([CH:17]=[O:18])[NH:8][C:7]=1[CH3:19])=[O:5])C.[OH-].[Na+].O>CO.CCOC(C)=O>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]1[C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:19])[NH:8][C:9]=1[CH:17]=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (300 mg, 1.13 mmol) and sodium hydroxide in MeOH (4 mL)/water (2 mL) was stirred at 80° C. for 19 hr. The reaction was then diluted with EtOAc. The aqueous layer was separated, neutralized and concentrated. The residue was dissolved in MeOH, filtered and the filtrate was concentrated to give 251 mg (94%) of 4-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid.

Workup

customThe aqueous layer was separated
concentrationconcentrated
dissolutionThe residue was dissolved in MeOH
filtrationfiltered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-cbebf8a6be8546749247328f611865ed
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531502B1

Linked notes

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