Ammonium Chloride → N-(2-amino-5-methylphenyl)benzamide

HRID 1888948Notes

Reaction equation

HRID 1888948 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[Cl-].[NH4+]>C(O)(C)C.[Fe]>[NH2:17][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=1[NH:8][C:9](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68517695N-(5-methyl-2-nitrophenyl)benzamide

Product 1

HCID 68519552N-(2-amino-5-methylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of N-(5-methyl-2-nitrophenyl)benzamide (3 mmol) in isopropanol (150 mL) was added iron powder (2 g) and ammonium chloride (0.3 mmol). The reaction mixture was heated at 100° C. for 12 h. The hot mixture was filtered off and the filtrate was evaporated. The residue was subjected to flash chromatography on silica gel using a mixture of hexanes and CH2Cl2 (9:1) as eluent to afford N-(2-amino-5-methylphenyl)benzamide as a white-gray solid.

Workup

  1. filtrationThe hot mixture was filtered off
  2. customthe filtrate was evaporated
  3. additiona mixture of hexanes and CH2Cl2 (9:1) as eluent

Sources & evidence

ORD record
ord-44e8f42250a549c8aaef025ddfca82bc
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

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