Allyl bromide → 6-(allyloxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023182ノート

反応式

HRID 1023182 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)[CH:20]=[CH2:19]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

生成物 1

HCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-one収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (1.5 g, 9.19 mmol) in DMF (20 mL), K2CO3 (2.54 g, 18.39 mmol) and allyl bromide (0.955 mL, 11.03 mmol) were added. The reaction mixture was stirred at room temperature for 3 h then concentrated. The residue was dissolved in ethyl acetate, washed with 10% NaOH solution, water, and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated to give 6-(allyloxy)-3,4-dihydroquinolin-2(1H)-one as a white solid (1.7 g, 89%). 1HNMR: 400 MHz, DMSO-d6: δ 2.40 (q, J=7.60 Hz, 2H), 2.83 (t, J=8.00 Hz, 2H), 4.48-4.50 (m, 2H), 5.22-5.26 (m, 1H), 5.35-5.40 (m, 1H), 5.97-6.07 (m, 1H), 6.72-6.80 (m, 3H), 9.89 (s, 1H), LCMS (ES-API), RT 1.566 min, m/z 204.2 (M+H).

後処理

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 10% NaOH solution, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-55766cf25ffb432ca94398d76cf16d0c
出典データセット
uspto-grants-2014_05
特許番号
US08722670B2

反応ノート

読み込み中…