Water → 6-Bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 530338노트

반응식

HRID 530338 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.C1C(=O)N([Br:21])C(=O)C1.O>CN(C=O)C.CCOC(C)=O>[Br:21][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[N:9]([CH3:12])[C:8](=[O:13])[CH2:7][CH2:6]2

참가 물질

6

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 224137757-Fluoro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

생성물 1

HCID 866791306-Bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one수율 78%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To an ice cold solution of 7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one (16.0 g, 89.4 mmol) in DMF (200 mL) was added NBS (16.0 g, 89.4 mmol). After the addition, the reaction mixture was warmed up to room temperature and stirred for 3 hr. After LC-MS analysis indicated the completion of reaction, the mixture was diluted with EtOAc (500 mL) and poured into water (500 mL). The aqueous layer was then extracted with EtOAc (200 mL, 3×) and the combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give crude title compound as oil (18.0 g, 78% yield). It was used in the next step without further purification.

후처리

  1. additionAfter the addition
  2. customthe completion of reaction
  3. extractionThe aqueous layer was then extracted with EtOAc (200 mL, 3×)
  4. washthe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8f62403e997c44fda0fd95b0449db12b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353081B2

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