Triethylamine → 6-Chloro-N-hydroxy-nicotinamidine

HRID 2242220Notes

Reaction equation

HRID 2242220 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1.Cl.[NH2:18][OH:19]>C(O)C>[Cl:8][C:9]1[N:10]=[CH:11][C:12]([C:13](=[N:18][OH:19])[NH2:14])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 336784996-Chloro-N-hydroxy-nicotinamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Triethylamine (68 mL, 498 mmol) was added to a solution of 6-chloronicotinonitrile (30.0 g, 217 mmol), hydroxylamine hydrochloride (33.0 g, 476 mmol) and ethanol (325 mL) and stirred for 12 hours at 75° C. The reaction mixture was cooled to room temperature, quenched with H2O (400 mL) and the partially concentrated in vacuo. The resulting slurry was filtered and dried to provide the title compound as a crude white solid (37.5 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with H2O (400 mL)
  3. concentrationthe partially concentrated in vacuo
  4. filtrationThe resulting slurry was filtered
  5. customdried

Sources & evidence

ORD record
ord-5e0e4a748aac4a9d903a8ace7258a9aa
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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