Water → 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 2219980노트

반응식

HRID 2219980 반응식
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]([C:16](=[O:18])[CH3:17])[CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 590215001-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone수율 92%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

To a stirred solution of 1,2,3,4-tetrahydro-4,4-dimethyl-7-nitroquinoline (Rami et al, WO 03/068749) (500 mg, 2.42 mmol), DMAP (5 mg) in pyridine (2 mL) was added acetic anhydride (0.46 mL, 4.9 mmol). The mixture was stirred at room temperature for 10 h, and then heated at 60° C. for 5 h. After cooling, the mixture was treated with water and extracted with EtOAc. The combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine, dried, and evaporated. The residue was purified by chromatography to give a light yellow solid (550 mg, 92%).

후처리

  1. temperatureheated at 60° C. for 5 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-3918ddff1ace42168345f296e94a4cec
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414131B2

반응 노트

불러오는 중…