Citric Acid → HCID 178436203, compound

HRID 1625862Notes

Reaction equation

HRID 1625862 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=2)=[N:9]1)=O)(C)(C)C.C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][N:9]=2)=[CH:23][CH:22]=1)[CH3:25]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 666081711h-Indazole-1-carboxylic acid,3-[(4-ethylphenyl)methyl]-,1,1-dimethylethyl ester

Product 1

HCID 178436203HCID 178436203, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above 1-t-butoxycarbonyl-3-(4-ethylphenylmethyl)-1H-indazole (1.35 g) was dissolved in methanol (15 ml), and added thereto was 28% sodium methoxide solution (methanol solution, 1.0 ml), and the mixture was stirred at room temperature for one hour. Added thereto was an aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from hexane to give the desired 3-(4-ethylphenylmethyl)-1H-indazole (800 mg) as colorless crystals. APCI-Mass m/Z 237 (M+H).

Workup

  1. additionadded
  2. additionAdded
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-d05ad05548c049d8a3c1001aefcdf949
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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