2-(Aminooxy)propionic acid hydrochloride → 7-(1-carboxyethoxyimino)-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267988Notes

Reaction equation

HRID 267988 reaction equation
Cl.[NH2:2][O:3][CH:4]([CH3:8])[C:5]([OH:7])=[O:6].[CH:9]1[C:18]2[N:19]3[C:23]([C:24](=O)[C:16]4[C:17]=2[C:12]([CH:13]=[CH:14][N:15]=4)=[CH:11][CH:10]=1)=[CH:22][CH:21]=[CH:20]3>O.C(O)C.N1C=CC=CC=1>[C:5]([CH:4]([O:3][N:2]=[C:24]1[C:16]2[C:17]3[C:12]([CH:13]=[CH:14][N:15]=2)=[CH:11][CH:10]=[CH:9][C:18]=3[N:19]2[C:23]1=[CH:22][CH:21]=[CH:20]2)[CH3:8])([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 208332742-(Aminooxy)propionic acid hydrochlorideHCID 215528757H-indolizino[5,6,7-ij]isoquinolin-7-one

Product 1

HCID 544352207-(1-carboxyethoxyimino)-7H-indolizino[5,6,7-ij]isoquinolineYield 76.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 2-aminooxypropionic acid hydrochloride (15.0 g.) in water (37.5 cc.) is added to a stirred boiling solution of 7H-indolizino[5,6,7-ij]isoquinolin- 7-one (15.0 g.) in ethanol (375 cc.) and pyridine (8.14 g.). Boiling is maintained for 2 hours 30 minutes. After cooling, the orange crystals are filtered off, washed with 90% ethanol, then with absolute ethanol and finally with diethyl ether. After drying, 7-(1-carboxyethoxyimino)-7H-indolizino[5,6,7-ij]isoquinoline (16.0 g.), melting at 225° C. with decomposition, is obtained.

Workup

  1. temperatureBoiling is maintained for 2 hours 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe orange crystals are filtered off
  4. washwashed with 90% ethanol
  5. customAfter drying

Sources & evidence

ORD record
ord-b908cae269cc47d5a67d06e6883292fd
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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