Ethyl Bromide → HCID 71255473, compound

HRID 540318Notes

Reaction equation

HRID 540318 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:14]=3[CH2:13]2)[CH:3]=1.[H-].[Na+].Br[CH2:27][CH3:28]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][C:21]([O:23][CH2:27][CH3:28])=[CH:22][C:14]=3[CH2:13]2)[CH:3]=1

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 86691442HCID 86691442, compound

Product 1

HCID 71255473HCID 71255473, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepin-8-ol (36 mg, 0.11 mmol) in 5 mL of dry N,N-dimethylformamide was added sodium hydride (8 mg, 0.17 mmol), then bromoethane (18.5 mg, 0.17 mmol) was added dropwise under nitrogen. After the addition, the reaction was stirred at room temperature for further 1 hour. The resulting mixture was diluted with dichloromethane (10 mL), washed with brine and then dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel to give 28 mg of product. MS obsd. (ESI+) [(M+H)+] 353.

Workup

  1. additionAfter the addition
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9633568dc3b2419bb9cfe0842c2cbfbe
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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