2-Chloro-5-nitroanisole → (S)-1-(2-Methoxy-4-nitrophenyl)-N-methylpyrrolidin-3-amine

HRID 1963032Notes

Reaction equation

HRID 1963032 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][NH:14][C@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1>>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:17]1[CH2:18][CH2:19][C@H:15]([NH:14][CH3:13])[CH2:16]1

Participants

3

Reactant 2

HCID 705192-Chloro-5-nitroanisoleHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidine

Product 1

HCID 58386150(S)-1-(2-Methoxy-4-nitrophenyl)-N-methylpyrrolidin-3-amine

Conditions

Temperature
130 °C

Procedure

A mixture of 1-chloro-2-methoxy-4-nitrobenzene (200 mg, 1.066 mmol) and (S)—N-methylpyrrolidin-3-amine (153 mg, 1.528 mmol) was heated at 130° C. in a sealed tube for 5 h. After cooling down to room temperature, the obtained black solid product (Example 41A) was used for next step without further purification. LCMS (ES): m/z 252.3 [M+H]+.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe obtained black solid product (Example 41A) was used for next step without further purification

Sources & evidence

ORD record
ord-e80206f4159f4b9989e66061d61eb56b
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

Loading…