Water → HCID 136398824, compound

HRID 1395224Notes

Reaction equation

HRID 1395224 reaction equation
[C:1]([C:3]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:4][NH:5][NH:6][C:7]1[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=[C:9]2[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:8]=12)#[N:2].O>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:21]([N:18]1[C:9]2[N:10]=[CH:11][C:12]3[C:13](=[O:14])[NH:2][C:1]4[N:6]([N:5]=[CH:4][C:3]=4[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]=3[C:8]=2[CH:20]=[N:19]1)[CH3:22]

Participants

5

Reactant 2

HCID 962WaterHCID 86736978HCID 86736978, compound

Product 1

HCID 136398824HCID 136398824, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

351 g of 4-[2-(2-cyano-3-ethoxy-3-oxo-1-propenyl)hydrazino]-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester are heated in 2 liters of acetic acid containing 50 g of zinc chloride for 24 hours. After this time, the solution is cooled and 2 liters of cold water are added. The precipitated 8-ethyl-5,8-dihydro-5-oxo-4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester is filtered off and purified by dissolving in the theoretical amount of sodium hydroxide in water and precipitating the compound with acetic acid, yield 256 g (83%); m.p. 263°-265°.

Workup

  1. temperatureAfter this time, the solution is cooled
  2. filtrationThe precipitated 8-ethyl-5,8-dihydro-5-oxo-4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester is filtered off
  3. custompurified
  4. dissolutionby dissolving in the theoretical amount of sodium hydroxide in water
  5. customprecipitating the compound with acetic acid, yield 256 g (83%)

Sources & evidence

ORD record
ord-2afcac306cc545cc857a3b3aff28596c
Source dataset
uspto-grants-1980_05
Patent number
US04202899

Reaction notes

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