N-bromobutanimide → 6-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

HRID 921968ノート

反応式

HRID 921968 の反応式
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

生成物 1

HCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (1-2; 8.30 g, 50.10 mmol) in N,N-dimethylformamide (250 mL) was added N-bromosuccinimide (9.80 g, 55.10 mmol) in N,N-dimethylformamide (120 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h, cooled, and diluted with ice cold water (500 mL). The resulting precipitated was filtered and dried to obtain the title compound as a white solid; 1H NMR (DMSO-D6, 500 MHz) δ=10.20 (s, 1H), 7.37 (dd, J=2.0 Hz, JHF=10.0 Hz, 1H), 7.26 (s, 1H), 2.93 (t, J=7.0 Hz, 2H), 2.47 (t, J=7.5 Hz, 2H).

後処理

  1. temperaturecooled
  2. customThe resulting precipitated
  3. filtrationwas filtered
  4. customdried

出典と根拠

ORDレコード
ord-99adc0e5d9be4277939bd3aa84790c69
出典データセット
uspto-grants-2016_03
特許番号
US09278093B2

反応ノート

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