Water → 7-methoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267994Notes

Reaction equation

[N+](=[CH2:3])=[N-].[C:4]([CH2:7][O:8][N:9]=[C:10]1[C:24]2[C:25]3[C:20]([CH:21]=[CH:22][N:23]=2)=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]2[C:11]1=[CH:12][CH:13]=[CH:14]2)([OH:6])=[O:5].O>C(OCC)C.CN(C)C=O>[CH3:3][O:5][C:4]([CH2:7][O:8][N:9]=[C:10]1[C:24]2[C:25]3[C:20]([CH:21]=[CH:22][N:23]=2)=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]2[C:11]1=[CH:12][CH:13]=[CH:14]2)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A 0.57M solution of diazomethane in diethyl ether (108 cc.) is added to a suspension of 7-carboxymethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline (15 g.) in dimethylformamide (150 cc.) cooled to 0° C. The mixture is kept at between 0° and 5° C. for 3 hours and is then allowed to return to a temperature of about 20° C. Water (450 cc.) is then added, the mixture is cooled in an ice-water bath and the yellow crystals thus obtained are filtered off. After drying, the crude methyl ester (14.17 g.) is obtained. After recrystallisation from ethyl acetate (280 cc.), the 7-methoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline obtained melts at 148 ° C. with decomposition.

Workup

customto return to a temperature of about 20° C
temperaturethe mixture is cooled in an ice-water bath
customthe yellow crystals thus obtained
filtrationare filtered off
customAfter drying
customthe crude methyl ester (14.17 g.) is obtained
customAfter recrystallisation from ethyl acetate (280 cc.)

Sources & evidence

ORD record: ord-868082771d034cf4abc8ffd0a26af0f1
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03946019

Reaction notes

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