Hydrochloric Acid → Methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate

HRID 2044026Notes

Reaction equation

HRID 2044026 reaction equation
Cl.[Cl:2][C:3]1[C:4]([N:9]2[C:13](O)([C:14]([O:16][CH3:17])=[O:15])[CH2:12][C:11]([CH2:19][OH:20])=[N:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1>CO>[Cl:2][C:3]1[C:4]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([CH2:19][OH:20])=[N:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54577408methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Product 1

HCID 53235501Methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of HCl (9.1 g, 4% solution in methanol) was added to the suspension of (28.5 g, 0.1 mol) of methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate in 100 ml of methanol. After ca. 30-60 min at 25-30° C., the clear yellow solution had formed. Methanol was removed in vacuo and the precipitate was washed with water. Yield 26.7 g, 100%. M.p. 104° C.

Workup

  1. customthe clear yellow solution had formed
  2. customMethanol was removed in vacuo
  3. washthe precipitate was washed with water

Sources & evidence

ORD record
ord-cd276a08d1a04d58ba106a4eed781e1a
Source dataset
uspto-grants-2013_11
Patent number
US08586753B2

Reaction notes

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