HCID 3097922, compound → 2-N-(4-Chlorophenyl)pyridine-2,3-diamine

HRID 2272700Notes

Reaction equation

HRID 2272700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 3097922HCID 3097922, compound

Product 1

HCID 124454222-N-(4-Chlorophenyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-chlorophenyl)-3-nitropyridin-2-amine (C8) (2.68 g, 10.7 mmol) in ethyl acetate (100 mL) was added Raney nickel (1.5 g), and the mixture was degassed with hydrogen. After 6 hours of hydrogenation at room temperature, the reaction mixture was filtered; concentration of the filtrate in vacuo afforded the product as a black solid. Yield: 1.8 g, 8.2 mmol, 77%. 1H NMR (400 MHz, DMSO-d6) δ 7.88 (br s, 1H), 7.67 (d, J=8.9 Hz, 2H), 7.50 (br d, J=4 Hz, 1H), 7.25 (d, J=8.9 Hz, 2H), 6.91 (br d, J=7.5 Hz, 1H), 6.64 (dd, J=7.3, 4.8 Hz, 1H), 5.08 (br s, 2H).

Workup

  1. customthe mixture was degassed with hydrogen
  2. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-7ddb124bc0294654ade419e10be2de00
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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