Hydrochloric Acid → 3-Amino-5-methoxy-[1,1'-biphenyl]-4-carboxamide

HRID 1519444ノート

反応式

HRID 1519444 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]#[N:9].[OH-:18].[K+].Cl>CCO>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]([NH2:9])=[O:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2 回HCID 867193553-Amino-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

生成物 1

HCID 867193563-Amino-5-methoxy-[1,1'-biphenyl]-4-carboxamide収率 40.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-amino-5-methoxy-[1,1′-biphenyl]-4-carbonitrile (4, 0.64 g, 2.86 mmol) and KOH (1.12 g, 20 mmol) in EtOH (24 mL) in a sealed tube was heated at 100° C. for 18 h. Additional KOH (0.56 g, 10 mmol) was added and heating was continued for another 18 h. After this time, the mixture was cooled to room temperature, and the pH was adjusted to ˜2 by addition of concentrated HCl. After concentration, the residue was partitioned between ethyl acetate (100 mL) and water (50 mL). The extracts were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with methanol in dichloromethane (0-20%) to afford the title compound (0.28 g, 40%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.62-7.60 (m, 2H), 7.58 (s, 1H), 7.47-7.44 (m, 2H), 7.39-7.36 (m, 1H), 7.28 (s, 1H), 6.61 (d, J=1.5 Hz, 1H), 6.56 (s, 2H), 6.43 (d, J=1.5 Hz, 1H), 3.87 (s, 3H); ESI MS m/z 243 [M+H]+.

後処理

  1. temperatureheating
  2. temperatureAfter this time, the mixture was cooled to room temperature
  3. concentrationAfter concentration
  4. customthe residue was partitioned between ethyl acetate (100 mL) and water (50 mL)
  5. washThe extracts were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with methanol in dichloromethane (0-20%)

出典と根拠

ORDレコード
ord-088feca568d240bf9bff5b232717569e
出典データセット
uspto-grants-2015_07
特許番号
US09073878B2

反応ノート

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