Methanol → Methyl 3-(chloromethyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

HRID 2070116Notes

Reaction equation

[ClH:1].[Cl:2][C:3]1[C:4]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([CH2:17]O)=[N:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)Cl.[CH3:23]O>C1(C)C=CC=CC=1>[Cl:1][CH2:17][C:11]1[CH:12]=[C:13]([C:14]([O:16][CH3:23])=[O:15])[N:9]([C:4]2[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][N:5]=2)[N:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(3-Chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylic acid hydrochloride 29 g (0.1 mol) was initially charged in 100 ml of toluene. 24 g SOCl2, was added in portions at 60° C. The mixture was heated at 70° C. for 3 h, in the course of which the precipitate went completely into the solution. Methanol (30 ml) was slowly added dropwise to the mixture and the solution was stirred at 30° C. for another hour. Subsequently, the solution was concentrated under reduced pressure. This afforded 95% of the product with a purity of 96%.

Workup

concentrationSubsequently, the solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-8ed85ddbbcb04a6c9174e91860af77dd
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299260B2

Reaction notes

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