Hydrochloric Acid → HCID 71087793, compound

HRID 1520773Notes

Reaction equation

HRID 1520773 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]([O:16]CC)=[O:15])[N:11]([CH3:19])[N:10]=2)=[CH:5][CH:4]=1)#[N:2].[Li+].[OH-].O.Cl>C1COCC1.CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]([CH3:19])[N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 71087904HCID 71087904, compound

Product 1

HCID 71087793HCID 71087793, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-cyanophenyl)-1-methyl-1H-pyrazole-5-carboxylate (70 mg, 274 μmol, Eq: 1.00) in THF (5 ml) and MeOH (1.00 ml) was added LiOH 1M (548 μl, 548 μmol, Eq: 2). The mixture was stirred for ca. 8 h at rt., then treated with water and HCl 1N (pH:3). The mixture was extracted two times with ethyl acetate. The resulting organic layers were combined, washed with Brine and dried over MgSO4, filtered and concentrated to give the desired compound (55 mg, 88.3%) as a white solid.

Workup

  1. extractionThe mixture was extracted two times with ethyl acetate
  2. washwashed with Brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee1da1e67b4742239379e92dcabadd61
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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