Methylamine → 6-Chloro-N-methylnicotinamide

HRID 1690142Notes

Reaction equation

HRID 1690142 reaction equation
[Cl:1][C:2]1[N:3](C)[CH2:4][C:5](=[CH:9][CH:10]=1)[C:6](Cl)=[O:7].CN.[CH2:14]([N:16](CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][CH3:14])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 86639403HCID 86639403, compound

Product 1

HCID 123642306-Chloro-N-methylnicotinamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-N-methylnicotinoyl chloride (7.39 g, 42.0 mmol) in tetrahydrofuran (50 mL), methylamine (42 mL, 84.0 mmol) and triethylamine (6.4 mL, 46.2 mmol) were added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was concentrated in vacuo, then filtered, and washed with tetrahydrofuran. The obtained residue was recrystallized (ethyl acetate/hexane) and 6-chloro-N-methylnicotinamide (6.52 g, yield 91%) was obtained as a white crystal.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated in vacuo
  3. filtrationfiltered
  4. washwashed with tetrahydrofuran
  5. customThe obtained residue was recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0a1ea1ce66944b9aa43ea5d6dfc6af62
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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