Sodium Hydroxide → HCID 66621889, compound

HRID 852922Notes

Reaction equation

HRID 852922 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:21])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]#[N:19])[C:15]([NH2:20])=[N:14]2)=[CH:8][CH:7]=1>O.CO>[NH2:20][C:15]1[C:16]([C:18]#[N:19])=[CH:17][N:13]([CH2:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:21])=[O:4])=[CH:7][CH:8]=2)[N:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666222814-(3-Amino-4-cyano-pyrazol-1-ylmethyl)-benzoic acid methyl ester

Product 1

HCID 66621889HCID 66621889, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of NaOH (343 mg, 8.58 mmol) in a mixture of water (10 ml) and MeOH (20 ml) the ester 95 (732 mg, 2.86 mmol) was added. The reaction mixture was refluxed 2 min and stirred for additional 2 hrs at ambient temperature. MeOH was removed under reduced pressure and remaining aqueous solution was acidified with conc. HCl (pH 3-4) to form a precipitate which was collected by filtration to afford the title compound (96) (640 mg, 92% yield). LRMS: 242.2 (calc.), 241.1 (found).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed 2 min
  3. customMeOH was removed under reduced pressure
  4. customto form a precipitate which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-dde82f7b0e724dfebac237b078681d02
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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