4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide → 3,4-diamino-N-(5,6-dimethylpyridin-2-yl)-benzamide

HRID 1514990Notes

Reaction equation

HRID 1514990 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=2)=[O:7])=[CH:4][C:3]=1[N+:19]([O-])=O.[H][H]>[Pt].C(OCC)(=O)C.C(O)C>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[NH2:1])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=1)=[O:7]

Participants

5

Reactant 2

HCID 669660594-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 669661333,4-diamino-N-(5,6-dimethylpyridin-2-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 4-amino-N-(5,6-dimethylpyridin-2-yl)-3-nitrobenzamide (470 mg, 1.64 mmol) and of 5% platinum on carbon (60 mg) in 50 mL of ethyl acetate/ethanol (1:1) was stirred in under a hydrogen balloon. When the reaction was complete by LC/MS, the mixture was filtered through Celite to remove catalyst, and the filtrate was removed under reduced pressure to afford 3,4-diamino-N-(5,6-dimethylpyridin-2-yl)-benzamide.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customto remove catalyst
  3. customthe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-2c893040fa4b46a0a7b196c0554be858
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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