3-Chloro-2-hydrazinylpyridine → methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

HRID 2044024Notes

Reaction equation

HRID 2044024 reaction equation
CC1(C)O[C:5](=[CH:7][C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10])[CH2:4][O:3]1.[NH:15]([C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=1)[NH2:16]>C(O)(C)C>[Cl:23][C:22]1[C:17]([N:15]2[C:8]([OH:13])([C:9]([O:11][CH3:12])=[O:10])[CH2:7][C:5]([CH2:4][OH:3])=[N:16]2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 5561003-Chloro-2-hydrazinylpyridineHCID 67235942Methyl 3-(2,2-dimethyl-1,3-dioxolan-4-ylidene)-2-oxopropanoate

Product 1

HCID 54577408methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
35 °C

Procedure

The mixture of methyl 3-(2,2-dimethyl-1,3-dioxolan-4-ylidene)-2-oxopropanoate (20 g, 0.1 mol) and 2-hydrazino-3-chloropyridine (14.3 g, 0.1 mol) in 40 ml of isopropanol was stirred for 18 hours at 35° C. The precipitate was filtered off and washed with 15 ml of isopropanol. This gave 24.2 g (85%) of the product as a pale yellow solid with a melting point of 113° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with 15 ml of isopropanol

Sources & evidence

ORD record
ord-09914f2e21e04dbe8631cc65c0d54874
Source dataset
uspto-grants-2013_11
Patent number
US08586753B2

Reaction notes

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