2-Methyl-3-nitrobenzamide → 3-Amino-2-methylbenzamide

HRID 6923Notes

Reaction equation

HRID 6923 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]>C(O)C.O1CCCC1.[C].[Pd]>[NH2:11][C:10]1[C:2]([CH3:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 1

HCID 38305922-Methyl-3-nitrobenzamide

Product 1

HCID 164957733-Amino-2-methylbenzamideYield 91.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-3-nitrobenzamide (8.85 g) was dissolved in a mixture solvent of ethanol (300 ml) and tetrahydrofuran (200 ml), followed by addition of 10% palladium-carbon (800 mg). The resulting mixture was stirred under hydrogen atmosphere at ambient temperature and atmospheric pressure for 6 hours. After insoluble materials were filtered off, the filtrate was concentrated under reduced pressure and washed with isopropyl ether, to afford the entitled compound as white solid (6.73 g, 91%). The physico-chemical values are as follows.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-0a904a1801944e218f386ef167711319
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Reaction notes

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