Benzyl Bromide → 1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 1267841노트

반응식

HRID 1267841 반응식
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13].CC(C)([O-])C.[K+].C1COCC1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.O.C(OC)(C)(C)C>[CH2:25]([N:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

8

반응물 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 127895324H-Imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 97952141-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 15413tert-Butyl methyl ether용매

실험 절차

A mixture of 4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I, J. Heterocyclic Chem., 19, 837-49 (1982), 1.0 g, 5.8 mmol) in DMF (10 ml) is cooled to 0° and treated with potassium t-butoxide in THF (1.98 M, 3.2 ml, 6.3 mmol) maintaining the reaction temperature at 0°. The resulting mixture is stirred at 0° for 10 minutes. Benzyl bromide (0.73 ml, 6.1 mmol) is then added while maintaining the reaction temperature at methyl t-butyl ether (MTBE) from water followed by several water washes. The MTBE phase is concentrated under reduced pressure. The concentrate is cooled to 0°, filtered and washed two times with 0° MTBE. The product is dried at 50° under reduced pressure with a nitrogen purge to give the title compound, CMR (CDCl3, 100 MHz) 153.78, 136.44, 128.69, 127.67, 127.60, 126.73, 125.86, 122.90, 122.78, 121.28, 116.92, 116.17, 108.36, 44.95 and 42.37 δ.

후처리

  1. temperatureis cooled to 0°
  2. temperaturemaintaining the reaction temperature at 0°
  3. concentrationThe MTBE phase is concentrated under reduced pressure
  4. temperatureThe concentrate is cooled to 0°
  5. filtrationfiltered
  6. washwashed two times with 0° MTBE
  7. customThe product is dried at 50° under reduced pressure with a nitrogen
  8. custompurge

출처 및 근거

ORD 기록
ord-a6413ad9201140f19789094c2e4632e6
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555548B2

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