Hydrochloric Acid → 2-Cyano-4-biphenylcarboxylic acid

HRID 423315Notes

Reaction equation

HRID 423315 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:2].C(O)C.[OH-].[Na+].Cl>CO.ClCCl.O>[C:1]([C:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 53846446Methyl 2-cyano-4-biphenylcarboxylate

Product 1

HCID 187797522-Cyano-4-biphenylcarboxylic acidYield 96.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To methyl 2-cyano-4-biphenylcarboxylate (D26) (935 mg, 3.94 mmol) was added ethanol (18 ml) but dissolution did not occur so dichloromethane (10 ml) was added. Sodium hydroxide (2 ml, 4.00 mmol) was then added and the reaction stirred for 2 h. To the mixture was added dichloromethane (20 mL) and 2M aqueous HCl (10 mL). The layers were separated and the aqueous extracted with further dichloromethane (20 mL). The combined organic phase was dried (phase separator) and the solvent removed in vacuo to give a white solid, which was dissolved in methanol (30 mL) and aqueous sodium hydroxide was added (2M, 3 mL). The reaction was stirred at room temperature for 1 h before addition of water (20 mL). The reaction was stirred for a further 1 h. Dichloromethane (60 mL) was added and the mixture shaken and the layers separated. The aqueous phase was extracted with further dichloromethane (50 mL) before the combined organic phase was dried (phase separator) and the solvent removed in vacuo to give the title compound as a white solid, (849 mg, 3.80 mmol). δH (d6-DMSO, 400 MHz): 13.60 (1H, br s), 8.38 (1H, d), 8.28 (1H, dd), 7.78 (1H, d), 7.63 (2H, m), 7.60-7.50 (3H, m). MS (ES): C14H9NO2 requires 223; found 222 (M−H+).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous extracted with further dichloromethane (20 mL)
  4. customThe combined organic phase was dried (phase separator)
  5. customthe solvent removed in vacuo
  6. customto give a white solid, which
  7. stirringThe reaction was stirred for a further 1 h
  8. stirringthe mixture shaken
  9. customthe layers separated
  10. extractionThe aqueous phase was extracted with further dichloromethane (50 mL) before the combined organic phase
  11. customwas dried (phase separator)
  12. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3551d4442bee480a905a1de47bbe7cdf
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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