Ethyl Acetate → 5-amino-2-methyl-N-(pyrimidin-5-yl)benzamide

HRID 2355096

Reaction equation

HRID 2355096 reaction equation
CCOC(C)=O.[CH3:7][C:8]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1)=[O:11].[H][H]>CO.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:8]([CH3:7])=[C:9]([CH:19]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][CH:16]=[N:15][CH:14]=1)=[O:11]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 248232552-methyl-5-nitro-N-(pyrimidin-5-yl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 248240475-amino-2-methyl-N-(pyrimidin-5-yl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 2 L high-pressure vessel was charged with Palladium 10% on carbon wet (50% water) and EtOAc (50 mL). 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide 45 (18.79 g) was dissolved in methanol (400 mL) and added to the previous mixture. The reaction vessel was pressurized to 30 psi of H2 and mechanically stirred until the hydrogen intake stopped. The reduction of the nitro group was complete by LCMS and the mixture was filtered off through paper and glass paper. The crude 5-amino-2-methyl-N-(pyrimidin-5-yl)benzamide 46 was obtained as a yellow solid and used without further purification.

Workup

  1. additionadded to the previous mixture
  2. filtrationthe mixture was filtered off through paper and glass paper

Sources & evidence

ORD record
ord-cf248572e410495aab32c2cbe1551cb3
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Linked notes

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