Ethyl aminoxyacetate hydrochloride → 7-Ethoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267990Notes

Reaction equation

HRID 267990 reaction equation
Cl.[NH2:2][O:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:10]1[C:19]2[N:20]3[C:24]([C:25](=O)[C:17]4[C:18]=2[C:13]([CH:14]=[CH:15][N:16]=4)=[CH:12][CH:11]=1)=[CH:23][CH:22]=[CH:21]3>O.C(O)C.N1C=CC=CC=1>[CH2:8]([O:7][C:5]([CH2:4][O:3][N:2]=[C:25]1[C:17]2[C:18]3[C:13]([CH:14]=[CH:15][N:16]=2)=[CH:12][CH:11]=[CH:10][C:19]=3[N:20]2[C:24]1=[CH:23][CH:22]=[CH:21]2)=[O:6])[CH3:9]

Participants

6

Reactant 2

HCID 12283957Ethyl aminoxyacetate hydrochlorideHCID 215528757H-indolizino[5,6,7-ij]isoquinolin-7-one

Product 1

HCID 543292267-Ethoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij]isoquinolineYield 56.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of ethyl aminooxyacetate hydrochloride (18.0 g.) in water (64 cc.) is added to a stirred boiling solution of 7H-indolizino[5,6,7-ij]isoquinolin-7-one (16.0 g.) in ethanol (320 cc.) and pyridine (9.1 g.). Boiling is maintained for 3 hours 30 minutes. After cooling, water (640 cc.) is added. The greenish yellow crystals thus obtained are filtered off and washed with 25% ethanol and then with water. After drying, crude 7-ethoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij isoquinoline (21.6 g.) is obtained and is recrystallised from a mixture of ethyl acetate (110 cc.) and cyclohexane (165 cc.). 7-Ethoxycarbonylmethoxyimino- 7H-indolizino[5,6,7-ij]isoquinoline (13.1 g.), melting at 134° C., is thus obtained.

Workup

  1. temperatureBoiling is maintained for 3 hours 30 minutes
  2. temperatureAfter cooling
  3. customThe greenish yellow crystals thus obtained
  4. filtrationare filtered off
  5. washwashed with 25% ethanol
  6. customAfter drying
  7. customcrude 7-ethoxycarbonylmethoxyimino-7H-indolizino[5,6,7-ij isoquinoline (21.6 g.) is obtained
  8. customis recrystallised from a mixture of ethyl acetate (110 cc.) and cyclohexane (165 cc.)

Sources & evidence

ORD record
ord-27748ffa94694f71bc8d34f6efb3a174
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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