Water → Nicotinamide

HRID 322029Notes

Reaction equation

HRID 322029 reaction equation
Cl.C[NH:3]OC.C(N(CC)CC)C.Cl[C:14]1[C:15](Cl)=[N:16][CH:17]=[C:18]([CH:22]=1)[C:19](Cl)=[O:20].O>ClCCl>[C:19]([NH2:3])(=[O:20])[C:18]1[CH:22]=[CH:14][CH:15]=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27821565,6-dichloropyridine-3-carbonyl Chloride

Product 1

HCID 936NicotinamideYield 167.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine hydrochloride (2.25 g, 0.023 mol) was slurried in dichloromethane (40 mL) and cooled in ice-acetone. Triethylamine (4.7 g, 0.047 mol) was then added dropwise, followed by a solution of 5,6-dichloronicotinoyl chloride (4.5 g, 0.021 mol) in dichloromethane (25 mL). The resultant mixture was allowed to warm to room temperature and stirred for one hour. Water (50 mL) was added and the mixture separated. The organic phase was washed with water, 1M hydrochloric acid, 10% sodium carbonate solution and brine. It was then dried (Na2SO4) and evaporated to dryness to give the desired product (4.3 g, 86%) as a yellow oil which crystallized on standing.

Workup

  1. customthe mixture separated
  2. washThe organic phase was washed with water, 1M hydrochloric acid, 10% sodium carbonate solution and brine
  3. dry with materialIt was then dried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bf28787e2a31403f8848ddfa235f10ea
Source dataset
uspto-grants-2001_04
Patent number
US06211202B1

Reaction notes

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