Lithium Hydroxide → HCID 67172375, compound

HRID 872891Notes

Reaction equation

HRID 872891 reaction equation
[C:1]([C:4]1[C:8]([Cl:9])=[C:7]([C:10]([O:12]C)=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2].[OH-].[Li+].S(=O)(=O)(O)[O-].[K+]>C1COCC1.O>[C:1]([C:4]1[C:8]([Cl:9])=[C:7]([C:10]([OH:12])=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 67170430HCID 67170430, compound

Product 1

HCID 67172375HCID 67172375, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture containing methyl 3-acetyl-4-chloro-1H-pyrazole-5-carboxylate (1.3 g, 0.0064 mol) in THF (30 ml), lithium hydroxide (1.35 g, 0.032 mol) in water (15 ml) was added dropwise at 5-10° C. The reaction mixture was stirred at RT for 18 h. Cold water (15 ml) was added and the pH was adjusted to ˜4 with 1N potassium bisulfate. The product was extracted with ethyl acetate, the organic layer dried with anhydrous Na2SO4 and concentrated. The crude product was purified by recrystallization from diethyl ether/n-hexane. Yield 56%. 1H-NMR (400 MHz; DMSO-d6): δ 2.57 (s, 3H), 13.91 (bs, 1H), 14.69 (s, 1H).

Workup

  1. additionwas added dropwise at 5-10° C
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialthe organic layer dried with anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by recrystallization from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-3ea23e745f0740eb9889c55af4449fa4
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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