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Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl ester → 1,2,4,7-Tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimdine-6-carboxylic acid, 1-methylethyl ester

HRID 1252990
Notes
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Reaction equation

HRID 1252990 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5](=[O:7])[CH:6]=1.[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([C:25](=O)[CH3:26])[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9]>CN(C)C=O.CCOCC>[CH3:26][C:25]1[NH:1][C:2]2[N:3]([NH:4][C:5](=[O:7])[CH:6]=2)[CH:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[C:18]=1[C:19]([O:21][CH:22]([CH3:23])[CH3:24])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 3951175Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl esterHCID 42555565-amino-3H-pyrazol-3-one

Product 1

HCID 141304321,2,4,7-Tetrahydro-5-methyl-7-(3-nitrophenyl)-2-oxopyrazolo[1,5-a]pyrimdine-6-carboxylic acid, 1-methylethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-5-pyrazolone (3.57 g; 36.1 mmole) and 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, 1-methylethyl ester (10.0 g; 36.1 mmole) in dry dimethylformamide (30 ml) was heated at 70° C. under argon for 24 hours. The reaction mixture was allowed to cool to room temperature and then diluted with ether. The resultant precipitate was filtered off and recrystallized from isopropanol to provide the title compound in crystalline form (4.23 g; melting point 254°-256° C.).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resultant precipitate was filtered off
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-40380c51587d4d338d8a63f849d3fef3
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04746656

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes