Aminooxyacetic acid hemihydrochloride → 7-carboxymethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267987Notes

Reaction equation

HRID 267987 reaction equation
Cl.[NH2:2][O:3][CH2:4][C:5]([OH:7])=[O:6].NO[CH2:10][C:11](O)=O.[CH:14]1[C:23]2[C:18](=[CH:19][CH2:20][C:21](=O)[CH:22]=2)[CH:17]=[CH:16][N:15]=1>O.C(O)C.N1C=CC=CC=1>[C:5]([CH2:4][O:3][N:2]=[C:20]1[C:16]2[C:10]3[C:11]([CH:23]=[CH:14][N:15]=2)=[CH:21][CH:22]=[CH:23][C:14]=3[N:15]2[C:19]1=[CH:18][CH:17]=[CH:16]2)([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 2723609Aminooxyacetic acid hemihydrochlorideHCID 67245344Isoquinoline-7-one

Product 1

HCID 537034467-carboxymethoxyimino-7H-indolizino[5,6,7-ij]isoquinolineYield 111.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of aminooxyacetic acid hemihydrochloride (60.0 g.) in water (180 cc.) is added to a stirred boiling solution of 7H-indolizino 5,6,7-ij]isoquinolin-7-one (60.0 g.) in ethanol (1,800 cc.) and pyridine (27.3 cc.). Boiling is maintained for 2 hours 30 minutes. After cooling, the yellow crystals obtained are filtered off, washed with 90% ethanol, then with absolute ethanol and finally with diethyl ether. After drying, 7-carboxymethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline (67.6 g.), melting at 212° C. with decomposition, is obtained.

Workup

  1. temperatureBoiling is maintained for 2 hours 30 minutes
  2. temperatureAfter cooling
  3. customthe yellow crystals obtained
  4. filtrationare filtered off
  5. washwashed with 90% ethanol
  6. customAfter drying

Sources & evidence

ORD record
ord-cc3828a225d4456ea65f0881f0978485
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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