Water → 6-bromo-2,2-dimethyl-1H-quinoline

HRID 20036

반응식

HRID 20036 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:13])([C:11]#[CH:12])[CH3:10])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O>[Cu]Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:9]([CH3:13])([CH3:10])[CH:11]=[CH:12]2

참가 물질

6

반응물 3

HCID 962WaterHCID 1140TolueneHCID 200822714-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

생성물 1

HCID 157119676-bromo-2,2-dimethyl-1H-quinoline

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine (3.30 g, 14 mmol) in toluene (14 ml, 14 mmol) was added copper(I) chloride (0.300 g, 3.0 mmol) in one portion. The reaction vessel was sealed and the resulting mixture was heated to 90 deg C. After stirring overnight, the mixture was transferred to a separatory funnel containing water and EtOAc. The aqueous layer was washed 1× with EtOAc and 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated. The crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH)) to provide the product. MS m/z: 238.

후처리

  1. customThe reaction vessel was sealed
  2. temperaturethe resulting mixture was heated to 90 deg C
  3. customthe mixture was transferred to a separatory funnel
  4. washThe aqueous layer was washed 1× with EtOAc and 3× with DCM
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))
  9. customto provide the product

출처 및 근거

ORD 기록
ord-d152b3b17a40462db5db14a623f944ac
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745484B2

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