Ammonium Hydroxide → 2-Chloronicotinamide

HRID 2396580Notes

Reaction equation

HRID 2396580 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+:14].[OH-].[NH4+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:7]([C:8]([NH2:14])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 2796614Ethyl chloronicotinate

Product 1

HCID 825882-ChloronicotinamideYield 50%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a mixture of ethyl 2-chloro-3-pyridinecarboxylate (1.85 g, 10 mmol), ammonium chloride (0.53 g, 10 mmol) and 15 mL of ammonium hydroxide (150 mmol) was added tetrabutylammonium bromide (0.32 g, 1 mmol). The mixture was stirred at ambient temperature for 18 hours, concentrated, washed with water and methanol, and dried to give 0.78 g (50%) of the title compound (m.p. 164°-166° C., uncorrected).

Workup

  1. concentrationconcentrated
  2. washwashed with water and methanol
  3. customdried

Sources & evidence

ORD record
ord-bb1a8d0921e348c3ad06810a79941362
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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