Methylamine → 6-Chloro-N-methylnicotinamide

HRID 1038508Notes

Reaction equation

HRID 1038508 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9]C=CC=1C(Cl)=O.[CH2:11]([N:13](CC)CC)C.CN.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[Cl:1][C:2]1[CH:21]=[CH:22][C:23]([C:24]([NH:13][CH3:11])=[O:20])=[CH:9][N:10]=1

Participants

5

Reactant 4

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 123642306-Chloro-N-methylnicotinamideYield 92%

Procedure

2-Chloronicotinoyl chloride (5.65 g, 32.1 mol) was dissolved in tetrahydrofuran (64 mL), added triethylamine (5.59 mL, 40.1 mol), and a solution of methylamine in tetrahydrofuran (20.1 mL, 40.1 mol) sequentially under ice-cold conditions, and stirred at room temperature for 3.5 hours. The reaction solution was concentrated in vacuo, recrystallized (ethyl acetate/hexane). The title compound (5.06 g (yield 92%)) was obtained as a light brown crystal.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d57f719e892a4160ae3ac9fb6c4a8c4e
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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