3-Hydrazinopyridine → Methyl 2-[5-(3-chlorophenyl)-3-methyl-1-(pyridin-3-yl)pyrazol-4-yl]acetate

HRID 888723

Reaction equation

[NH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[NH2:2].[Cl:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([CH:15]([C:21](=O)[CH3:22])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=O>C(O)C>[Cl:9][C:10]1[CH:11]=[C:12]([C:13]2[N:1]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)[N:2]=[C:21]([CH3:22])[C:15]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

0.577 g (4.233 mmol) of 3-hydrazinopyridine in 5.00 ml of ethanol was added to 0.650 g (2.419 mmol) of methyl 3-(3-chlorobenzoyl)-4-oxopentanoate, and the mixture was stirred in a closed vessel in a microwave oven at 130° C. for 1.5 h. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane and washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.364 g (42% of theory) of a light-yellow oil. 1H-NMR (CDCl3): see Table 2.

Workup

customThe solvent was removed under reduced pressure
washwashed twice with in each case 25 ml of water
dry with materialThe combined organic phases were dried over sodium sulfate
customthe solvent was removed under reduced pressure
customChromatography of the residue gave 0.364 g (42% of theory) of a light-yellow oil

Sources & evidence

ORD record: ord-76739736b14c447e83fa235c27e92d13
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252723B2

Linked notes

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