(2-Nitrophenyl)-pyrimidin-2-yl-amine → N-Pyrimidin-2-yl-benzene-1,2-diamine

HRID 1599078Notes

Reaction equation

HRID 1599078 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([O-])=O.[H][H]>CCOC(C)=O.CO.[Ni]>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 14819593(2-Nitrophenyl)-pyrimidin-2-yl-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 14819594N-Pyrimidin-2-yl-benzene-1,2-diamineYield 72.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-nitrophenyl)-pyrimidin-2-yl-amine (13.2 g, 61.1 mmol) in a mixture of EtOAc (450 mL) and CH3OH (350 mL) was added Raney Nickle (16 g (water wet)) and the reaction mixture hydrogenated under 1 atm hydrogen at ambient temperature for 3 h. The catalyst was separated by filtration and the filtrate concentrated in vacuo to a red-brown solid which upon trituration with cold CH3OH (250 mL) gave the title compound (8.21 g, 44.1 mmol) as a grey solid: 1H NMR (CDCl3, 400 MHz): 8.38 (d, 2H, J=4.9 Hz), 7.37 (d, 1H, J=7.9 Hz), 7.08 (t, 1H), 7.00 (br s, 1H), 6.83 (m, 2H), 6.67 (t, 1H), 3.60 (br s, 2H); TLC (EtOAc/Hexanes(2:1)): Rf =0.33.

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe filtrate concentrated in vacuo to a red-brown solid which upon trituration with cold CH3OH (250 mL)

Sources & evidence

ORD record
ord-1df35c30871d4246940c142dab1719c5
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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