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

HRID 267982Notes

Reaction equation

HRID 267982 reaction equation
[CH:1]1[C:10]2[N:11]3[C:15]([C:16](=O)[C:8]4[C:9]=2[C:4]([CH:5]=[CH:6][N:7]=4)=[CH:3][CH:2]=1)=[CH:14][CH:13]=[CH:12]3.Cl.[NH2:19][OH:20].O>N1C=CC=CC=1>[OH:20][N:19]=[C:16]1[C:8]2[C:9]3[C:4]([CH:5]=[CH:6][N:7]=2)=[CH:3][CH:2]=[CH:1][C:10]=3[N:11]2[C:15]1=[CH:14][CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 215528757H-indolizino[5,6,7-ij]isoquinolin-7-one

Product 1

HCID 1363535147-hydroxyimino-7H-indolizino[5,6,7-ij]isoquinolineYield 90.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7H-indolizino[5,6,7-ij]isoquinolin-7-one (28 g.) and hydroxylamine hydrochloride (28 g.) in pyridine (560 cc.) is maintained at the boiling point, with stirring. The brown solution thus obtained is poured into water (3.92 liters). After stirring for 3 hours, the mustard yellow crystals obtained are filtered off and then washed copiously with water. After drying, 7-hydroxyimino-7H-indolizino[5,6,7-ij]isoquinoline (27.2 g.), melting at 254° C. with decomposition, is obtained. After recrystallisation from a mixture of water and pyridine (6- 5 by volume), the pure product melts at 258° C. with decomposition.

Workup

  1. customThe brown solution thus obtained
  2. stirringAfter stirring for 3 hours
  3. customthe mustard yellow crystals obtained
  4. filtrationare filtered off
  5. washwashed copiously with water
  6. customAfter drying

Sources & evidence

ORD record
ord-d46f2a13818c499691fb0d3e26646312
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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