(2-Aminophenyl)(3-methoxyphenyl)methanone → 2-Amino-3'-hydroxybenzophenone

HRID 1870730ノート

反応式

HRID 1870730 の反応式
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[CH:7]=1)=[O:5]>Br>[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=[O:5]

参加物

3

反応物 1

HCID 22135242(2-Aminophenyl)(3-methoxyphenyl)methanone

生成物 1

HCID 186932032-Amino-3'-hydroxybenzophenone収率 92.7%

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

実験手順

2-Amino-3'-methoxybenzophenone (6.92 g, 30.5 mmol) was dissolved in 125 mL of 48% hydrobromic acid and the solution was heated at refluxed for 12 h. The solvent was removed by rotary evaporation and the resulting red solid was distributed between saturated sodium bicarbonate (400 mL) and CH2Cl2 (500 mL). The aqueous layer was washed with CH2Cl2 (2×100 mL) and the combined organic layers were dried with sodium sulfate and concentrated in vacuo to afford 6.03 g (92% yield) of 2-amino-3'-hydroxybenzophenone as a red oil. Recrystalization from ethyl acetate/hexanes (reflux, 4° C.) provided light red crystals: mp 130-132° C., Rf 0.25 (75:25, hexanes/ethyl acetate). 1H NMR (500 MHz, CDCl3) δ 5.25 (b, 1), 6.06 (b, 2), 6.58 (dt, 1, J=1.0, 7.5), 6.72 (d, 1, J=8.2), 6.98 (dd, 1, J=2.2, 8.2), 7.07 (t, 1, J=2.0), 7.15 (d, 1, J=7.5), 7.28 (m, 2), 7.45 (dd, 1, J=1.5, 8.0). 13C NMR (101 MHz): δ 77.2, 115.6, 115.7, 117.0, 118.2, 121.7, 129.4, 134.4, 134.6, 141.6, 150.9, 155.4. HRMS (FAB, m-nitrobenzyl alcohol) calcd for C13H11NO2 (M+H) 214.0843, found 214.0867.

後処理

  1. temperaturethe solution was heated
  2. temperatureat refluxed for 12 h
  3. customThe solvent was removed by rotary evaporation
  4. washThe aqueous layer was washed with CH2Cl2 (2×100 mL)
  5. dry with materialthe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-56a1b102f4c64227804347b45b81cf4f
出典データセット
uspto-grants-2000_08
特許番号
US06100254

反応ノート

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