Water → HCID 15640831, compound

HRID 256690Notes

Reaction equation

HRID 256690 reaction equation
N[CH:2]1[N:6]2[C:7](=[O:20])[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:5]2[C:4]2[S:21][CH:22]=[CH:23][C:3]1=2.O>C(O)(=O)C.[Zn]>[O:20]=[C:7]1[N:6]2[CH2:2][C:3]3[CH:23]=[CH:22][S:21][C:4]=3[C:5]2=[C:10]([C:11]([OH:13])=[O:12])[CH:9]=[C:8]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 962WaterHCID 15640830HCID 15640830, compound

Product 1

HCID 15640831HCID 15640831, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A suspension of 45.7 g of 4-amino-4,6-dihydro-6-oxo-7-phenylthieno[2',3':3,4]pyrrolo [1,2-a]pyridine-9-carboxylic acid in 915 ml of acetic acid was treated with 27.6 g of zinc powder and heated to boiling under reflux for 2 hours. The suspension was then cooled and poured into 3000 ml of water. The excess zinc was for the most part removed by decantation. The separated crystals were filtered off under suction and dried in a vacuum. There was obtained 42.4 g of 4,6-dihydro-6-oxo-7-phenylthieno[2',3':3,4]-pyrrolo[1,2-a]pyridine-9-carboxylic acid with a m.p. of >300° (purity 85-90%). This material was purified further by recrystallization from methanol/N,N-dimethylformamide.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe suspension was then cooled
  4. customremoved by decantation
  5. filtrationThe separated crystals were filtered off under suction
  6. customdried in a vacuum

Sources & evidence

ORD record
ord-8a05f6d31d5848e186a3f579383b8856
Source dataset
uspto-grants-1993_11
Patent number
US05258387

Reaction notes

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