Pyridoxal 5'-phosphate monohydrate → 5-Amino-N-(4-bromo-phenyl)-2-methyl-benzamide

HRID 1846116Notes

Reaction equation

HRID 1846116 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[CH3:19])=[CH:4][CH:3]=1.CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.O>[Ni].C(Cl)Cl.CCO>[NH2:16][C:14]1[CH:13]=[CH:12][C:11]([CH3:19])=[C:10]([CH:15]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:20]

Participants

5

Reactant 2

HCID 38882Pyridoxal 5'-phosphate monohydrateHCID 47364174N-(4-bromo-phenyl)-2-methyl-5-nitro-benzamide

Product 1

HCID 584834745-Amino-N-(4-bromo-phenyl)-2-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to example 2e with N-(4-bromo-phenyl)-2-methyl-5-nitro-benzamide (0.18 g; 0.54 mmol) and Ra-Ni (20 mg), 3 bar H2. Yield: 0.14 g (85%) MS: [m+H]+=305; HPLC Rt=1.2 min (Method MC-1); TLC (silica gel; DCM/EtOH 95/5) Rf=0.3

Sources & evidence

ORD record
ord-0835278b40b84074b0ac4e22a171e192
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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