N-(4-Bromophenyl)-2-methoxy-5-nitro-benzoic acid amide → N-(4-Bromophenyl)-2-methoxy-5-amino-benzoic acid amide

HRID 1846082Notes

Reaction equation

HRID 1846082 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[O:19][CH3:20])=[CH:4][CH:3]=1>C1COCC1.[Ni]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=2[O:19][CH3:20])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 9042746N-(4-Bromophenyl)-2-methoxy-5-nitro-benzoic acid amide

Product 1

HCID 61090759N-(4-Bromophenyl)-2-methoxy-5-amino-benzoic acid amide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-bromophenyl)-2-methoxy-5-nitro-benzoic acid amide (930 mg, 2.6 mmol) and 140 mg Ra-Ni in 40 mL THF was stirred for 20 h under an atmosphere of hydrogen (3 bar). After filtration and concentration i. vac. the subtitle compound was obtained. Yield: 890 mg (quantitative). MS [M+H]+=321 (Br-isotope pattern); TLC: Rf=0.60 (silica gel, DCM:EtOH 9:1).

Workup

  1. filtrationAfter filtration and concentration i

Sources & evidence

ORD record
ord-6577e1dc29e54781a7bbfac0bf3aeeae
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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