Hydroquinone → 4-(3-(Methyl(phenyl)amino)propoxy)phenol

HRID 1053574ノート

反応式

HRID 1053574 の反応式
Br[CH2:2][CH2:3][CH2:4][N:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1([CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1)[OH:20]>CN(C=O)C>[CH3:12][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][CH2:3][CH2:2][O:20][C:19]1[CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 61288549N-(3-bromopropyl)-N-methylaniline

生成物 1

HCID 717359274-(3-(Methyl(phenyl)amino)propoxy)phenol収率 24.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of compound 9a (500 mg, 2.7 mmol), K2CO3 (740 mg, 5.4 mmol), and KI (445 mg, 2.7 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (589 mg, 5.4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hours. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mLs water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with CH2Cl2 and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the compound 9 (170 mg, 0.66 mmol, 24% yield) as a white solid. HRMS (ESI, positive) m/z calcd. for C16H20NO2 [M+H]+: 258.14886, found: 258.14888. 1H NMR (400 MHz, Chloroform-d) δ 7.36-7.27 (m, 2H), 6.94-6.70 (m, 7H), 5.94 (broad s, 1H), 4.00 (t, J=5.9 Hz, 2H), 3.60 (t, J=7.0 Hz, 2H), 3.01 (s, 3H), 2.09 (p, J=6.2 Hz, 2H).

後処理

  1. additionwas added to the mixture under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mLs water
  6. extractionThe mixture was then extracted with CH2Cl2
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine and was dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography with hexane/EtOAc

出典と根拠

ORDレコード
ord-3ed6e073011b4103a6d62e36e81689fa
出典データセット
uspto-grants-2016_07
特許番号
US09394233B2

反応ノート

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