Ammonium Chloride → 2-Amino-4-methylbenzamide

HRID 1469757Notes

Reaction equation

HRID 1469757 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 132443694-Methyl-2-nitrobenzamide

Product 1

HCID 28014742-Amino-4-methylbenzamideYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared following the procedure described in Step 3 of Intermediate-1 using 4-methyl-2-nitrobenzamide (1.60 g, 8.88 mmol), iron powder (2.97 g, 53.33 mmol), and NH4Cl (2.85 g, 53.33 mmol) in EtOH (8 mL) and water (2 mL) to afford 1.2 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 7.62 (br s, 1H), 7.42 (d, J=7.8 Hz, 1H), 6.93 (br s, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.29 (d, J=7.8 Hz, 1H), 2.15 (s, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a76ae8ec28024383bf3999fe1720b971
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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