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

HRID 1521671노트

반응식

HRID 1521671 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 (157-2; 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. Reaction mixture was allowed to stir at room temperature for 18 h, then cooled and diluted with ice cold water (500 mL). The resulting precipitated was filtered and dried to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=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. customReaction mixture
  2. temperaturecooled
  3. customThe resulting precipitated
  4. filtrationwas filtered
  5. customdried

출처 및 근거

ORD 기록
ord-d954e5f298b14c0b87995107325d6721
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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