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Pyruvic Acid → 2,6-Dimethyl-4-(1-phenyl-1H-pyrazol-3-yl)aminophenyl 2-oxopropanoate

HRID 22278
Notes
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Reaction equation

HRID 22278 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[O:15].[CH3:19][C:20]1[CH:25]=[C:24]([NH:26][C:27]2[CH:31]=[CH:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:28]=2)[CH:23]=[C:22]([CH3:38])[C:21]=1O>ClCCl>[O:15]=[C:14]([CH3:16])[C:13]([O:18][C:21]1[C:22]([CH3:38])=[CH:23][C:24]([NH:26][C:27]2[CH:31]=[CH:30][N:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:28]=2)=[CH:25][C:20]=1[CH3:19])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 199279132,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl) aminophenol

Product 1

HCID 199279362,6-Dimethyl-4-(1-phenyl-1H-pyrazol-3-yl)aminophenyl 2-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1'-carbonyldiimidazole (4.9 g) was added batchwise to pyruvic acid (2.6 g) in dichloromethane (100 ml), and after 0.5 hours 2,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl) aminophenol (2.8 g) was added. The mixture was left for 16 hours, then evaporated, and the residue was chromatographed (silica, dichloromethane) to give, after crystallisation (hexane/ethyl acetate), the title product (1.0 g) mp 123°-125°.

Workup

  1. customevaporated
  2. customthe residue was chromatographed (silica, dichloromethane)
  3. customto give
  4. customafter crystallisation (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-53b23d7d80234aec8d63a40301135afd
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428044

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes