Triethylamine → (5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone

HRID 1904685

Reaction equation

HRID 1904685 reaction equation
[C:1]1([CH:7]2[NH:11][N:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>C(Cl)(Cl)Cl>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([N:11]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH:9]=[N:10]2)=[O:27])[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 3078467(5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanoneYield 86.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-phenyl-2-pyrazoline (2.9 g) and triethylamine (4 g) was added dropwise with ice cooling to a suspension of nicotinoyl chloride hydrochloride (4 g) in 20 ml chloroform, the resulting mixture was stirred for 15 minutes, washed with water and concentrated, and the concentrate was purified by silica gel chromatography (chloroform/methanol=100/1), giving 4.3 g (yield: 86%) of pure product. M.p. 100°-102° C.; NMR (CDCl3): 2.9-3.8 (2H, m), 5.61 (1H, dd, J=5, 12 Hz), 7.03 (1H, t, J=2 Hz), 7.31 (5H, s), 7.28 (1H, m), 8.15 (1H, dt, J=8, 2 Hz), 8.68 (1H, dd, J=2, 6 Hz), 9.13(1H, d, J=2 Hz).

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customthe concentrate was purified by silica gel chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-6d56b42708264f458ab9c8c2ec6083c0
Source dataset
uspto-grants-1989_06
Patent number
US04839376

Linked notes

Loading…