Hydrochloric Acid → 2-Cyano-4-biphenylcarboxylic acid

HRID 423315ノート

反応式

HRID 423315 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 187797522-Cyano-4-biphenylcarboxylic acid収率 96.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-3551d4442bee480a905a1de47bbe7cdf
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

反応ノート

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