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

HRID 267992Notes

Reaction equation

HRID 267992 reaction equation
Cl.[NH2:2][O:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[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:6]([CH2:5][CH2:4][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)([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 126043173-(Aminooxy)propanoic acid hydrochlorideHCID 215528757H-indolizino[5,6,7-ij]isoquinolin-7-one

Product 1

HCID 542889217-(2-carboxyethoxyimino)-7H-indolizino[5,6,7-ij]isoquinolineYield 75.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 3-aminooxypropionic acid hydrochloride (12 g.) in water (36 cc.) is added to a stirred boiling solution of 7H-indolizino[5,6,7-ij]isoquinolin-7-one (12 g.) in ethanol (360 cc.) and pyridine (6.64 g.). Boiling is maintained for 3 hours 10 minutes. After cooling, the yellow crystals obtained are filtered off and then washed with 90% ethanol, with absolute ethanol and finally with diethyl ether. After drying, 7-(2-carboxyethoxyimino)-7H-indolizino[5,6,7-ij]isoquinoline (12.59 g.), melting at 250° C. with decomposition, is obtained.

Workup

  1. temperatureBoiling is maintained for 3 hours 10 minutes
  2. temperatureAfter cooling
  3. customthe yellow crystals obtained
  4. filtrationare filtered off
  5. washwashed with 90% ethanol, with absolute ethanol and finally with diethyl ether
  6. customAfter drying

Sources & evidence

ORD record
ord-8afcfd7615674657a28a1b63174ef5fb
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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