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

HRID 530338ノート

反応式

HRID 530338 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8f62403e997c44fda0fd95b0449db12b
出典データセット
uspto-grants-2016_05
特許番号
US09353081B2

反応ノート

読み込み中…