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

HRID 20036

反応式

HRID 20036 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d152b3b17a40462db5db14a623f944ac
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

関連ノート

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