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

HRID 1870730노트

반응식

HRID 1870730 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

HCID 186932032-Amino-3'-hydroxybenzophenone수율 92.7%

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56a1b102f4c64227804347b45b81cf4f
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100254

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