7H-indolizino[5,6,7-ij]isoquinolin-7-one → 7-(alpha-carboxybenzyloxyimino)-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267989Notes

Reaction equation

HRID 267989 reaction equation
Cl.[NH2:2][O:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].[CH:14]1[C:23]2[N:24]3[C:28]([C:29](=O)[C:21]4[C:22]=2[C:17]([CH:18]=[CH:19][N:20]=4)=[CH:16][CH:15]=1)=[CH:27][CH:26]=[CH:25]3>O.C(O)C.N1C=CC=CC=1>[C:5]([CH:4]([O:3][N:2]=[C:29]1[C:21]2[C:22]3[C:17]([CH:18]=[CH:19][N:20]=2)=[CH:16][CH:15]=[CH:14][C:23]=3[N:24]2[C:28]1=[CH:27][CH:26]=[CH:25]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 215528757H-indolizino[5,6,7-ij]isoquinolin-7-oneHCID 68140601alpha-Aminooxyphenylacetic acid hydrochloride

Product 1

HCID 540076077-(alpha-carboxybenzyloxyimino)-7H-indolizino[5,6,7-ij]isoquinolineYield 70.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of α-aminooxyphenylacetic acid hydrochloride (15.0 g.) in water (6.6 cc.) is added to a stirred boiling solution of 7H-indolizino[5,6,7-ij]isoquinoline-7-one (15.0 g.) in ethanol (450 cc.) and pyridine (583 g.). Boiling is maintained for 2 hours 30 minutes. After cooling, the yellow crystals obtained are filtered off and then washed with 90% ethanol, then with absolute ethanol and finally with diethyl ether. After drying, 7-(α-carboxybenzyloxyimino)-7H-indolizino[5,6,7-ij]isoquinoline (17.7 g.), melting at 200° 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-5de9007e615547b4b727b3b21a93fab7
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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