Water → n-Methyl-3-nitropyridin-4-amine

HRID 1467700Notes

Reaction equation

HRID 1467700 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][NH2:12].O>ClCCl>[CH3:11][NH:12][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 556016n-Methyl-3-nitropyridin-4-amineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 4-chloro-3-nitropyridine (2 g, 12.6 mmol) in dichloromethane (15 mL) was cautiously added methyl amine (25% solution in water, 10 mL, 63 mmol). The reaction mixture was heated to 40° C. After stirring for 1 h, the mixture was poured into water (20 mL), and the precipitate was collected by filtration and dried in vacuo to afford the title compound (1.9 g, yield 98%) as a yellow solid. LC-MS (ESI) m/z: 154 (M+1)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-70535f04388d410f80c351a516c36667
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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