Hydrochloric Acid → HCID 71087897, compound

HRID 1520775Notes

Reaction equation

HRID 1520775 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[NH:13][N:12]=[C:11]([C:14]([O:16]CC)=[O:15])[C:10]=2C)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Li+].[OH-].O.Cl.[CH2:24]1COCC1>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[N:12]([CH3:24])[N:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178470498HCID 178470498, compound

Product 1

HCID 71087897HCID 71087897, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-(3-cyanophenyl)-4-methyl-1H-pyrazole-3-carboxylate (100 mg, 392 μmol, Eq: 1.00) in THF (5 ml) in MeOH (1.00 ml) was added LiOH 1M (2.35 ml, 2.35 mmol, Eq: 6). The mixture was stirred overnight. To the residue was added water and HCl 1N (pH:1), this aqueous phase was extracted two times with ethyl acetate, the resulting organic layers were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the desired compound (52 mg, 52.6%) as a yellow solid. MS (ISP): 228.1 (M+1).

Workup

  1. extractionthis aqueous phase was extracted two times with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-137c7776c4a6464fa4fa0b537873e229
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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