2-Bromo-5-nitropyridine → N-methyl-1-(5-nitropyridin-2-yl)pyrrolidin-3-amine

HRID 1963028Notes

Reaction equation

HRID 1963028 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.Br[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1>>[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 782402-Bromo-5-nitropyridineHCID 117882683-(Methylamino)pyrrolidine

Product 1

HCID 58386059N-methyl-1-(5-nitropyridin-2-yl)pyrrolidin-3-amine

Conditions

Temperature
110 °C

Procedure

N-methylpyrrolidin-3-amine (0.395 g, 3.94 mmol) was added to 2-bromo-5-nitropyridine (0.8 g, 3.94 mmol) slowly (CAUTION: extreme exotherm!!!). The resulting mixture was heated at 110° C. for 2 h. After cooling down to room temperature, the obtained black solid product (Example 16A, 0.87 g, 99%) was used for next step without further purification. LCMS (ES): m/z 233.4 [M+H]+.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe obtained black solid product (Example 16A, 0.87 g, 99%) was used for next step without further purification

Sources & evidence

ORD record
ord-ee71cc2de1e84213a058948fad49f314
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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