Water → HCID 22750102, compound

HRID 2164046Notes

Reaction equation

HRID 2164046 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:15]([OH:17])=O)=[CH:5][N:6]=[C:7]2[O:12][CH2:13][CH3:14].CO[CH:20]1[CH2:24][CH2:23][CH:22](OC)O1.O>C(O)(=O)C>[CH2:13]([O:12][C:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]3[N:1]4[C:20]([C:15](=[O:17])[C:4]([C:3]=23)=[CH:5][N:6]=1)=[CH:24][CH:23]=[CH:22]4)[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 790982,5-DimethoxytetrahydrofuranHCID 22750089HCID 22750089, compound

Product 1

HCID 22750102HCID 22750102, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 5-amino-4-carboxy-1-ethoxyisoquinoline (50.8 g) and 2,5-dimethoxytetrahydrofuran (32 cc) in acetic acid (250 cc) is kept at a temperature between 90° and 95° C. for 35 minutes, whilst stirring. The solution is cooled to about 20° C. and then poured into water (1250 cc). The yellow crystals which precipitate are filtered off and washed with water (5 × 50 cc). After drying under reduced pressure (1 mm Hg) at 20° C., crude 4-ethoxy-7-oxo-7H-indolizino[7,6,5-de]isoquinoline (52.7 g) is obtained. After recrystallisation from ethanol, the pure product melts at 188° C.

Workup

  1. filtrationThe yellow crystals which precipitate are filtered off
  2. washwashed with water (5 × 50 cc)
  3. customAfter drying under reduced pressure (1 mm Hg) at 20° C.

Sources & evidence

ORD record
ord-403ce0ceca2948f79e482928574ced67
Source dataset
uspto-grants-1979_01
Patent number
US04137315

Reaction notes

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