Cyclopropanemethanamine → HCID 55138170, compound

HRID 643699Notes

Reaction equation

HRID 643699 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:16][CH2:15][CH:12]2[CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 55138170HCID 55138170, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-2-chloro-3-nitropyridine (Step B, 5.0 g, 21.1 mmol), cyclopropanemethylamine (2.8 mL, 31.7 mmol) and N,N-diisopropylethylamine (5.5 mL, 31.7 mmol) in ethanol (20 mL) was stirred at room temperature for 24 h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate as eluent) to afford the title compound (5.5 g, 96%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-e004f284f5504072ba251c6d42ac221a
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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