Triethylamine → HCID 73990601, compound

HRID 2415759Notes

Reaction equation

HRID 2415759 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]#[N:13])[CH:11]=1)=[O:5])[CH3:2].Cl.[NH2:15][OH:16].C(N(CC)CC)C>CO>[NH2:13][C:12](=[N:15][OH:16])[C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH:11]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 359390Ethyl 5-cyanonicotinateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73990601HCID 73990601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl-(5-cyano-3-pyridyl)carboxylate) (WO 96/30372) (1.8 g, 10.2 mmol) was dissolved in methanol (50 mL), the solution was cooled to 0° C. then hydroxylamine hydrochloride (0.71 g, 10.2 mmol) and triethylamine (1.4 mL, 10.2 mmol) were added and the mixture was stirred at room temperature for 72 hours. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel (graded elution of dichloromethane/methanol 95:5 to 93:7) to give the title compound as a white solid which contained 0.3 equivalents of triethylamine hydrochloride (2.5 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel (graded elution of dichloromethane/methanol 95:5 to 93:7)

Sources & evidence

ORD record
ord-b3734df8c6e445969b89826a78e67c86
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

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