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

HRID 20036

Reaction equation

HRID 20036 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d152b3b17a40462db5db14a623f944ac
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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