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

HRID 921968노트

반응식

HRID 921968 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-99adc0e5d9be4277939bd3aa84790c69
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278093B2

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