Ethyl bromoacetate → 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 2418767Notes

Reaction equation

HRID 2418767 reaction equation
[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[OH-].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]1=[O:13]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 27571843-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 133399633-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (300 mg) was added in one portion to a stirred suspension of potassium hydroxide (90 mg) and tetrabutylammonium bromide (40 mg) in tetrahydrofuran (10 ml) maintained at 0° under a nitrogen atmosphere. Stirring was continued for 5 minutes, then ethyl bromoacetate (200 mg) was added in one portion. The reaction mixture was allowed to warm to room temperature while stirring for an additional 3 hours. The tetrahydrofuran was removed under reduced pressure and the residue partitioned between water (5 ml) and ether (25 ml). The organic phase was washed with 2N hydrochloric acid (5ml), dried over magnesium sulfate, and the solvent removed under reduced pressure to give 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. 114°-116°.

Workup

  1. temperaturemaintained at 0° under a nitrogen atmosphere
  2. stirringwhile stirring for an additional 3 hours
  3. customThe tetrahydrofuran was removed under reduced pressure
  4. customthe residue partitioned between water (5 ml) and ether (25 ml)
  5. washThe organic phase was washed with 2N hydrochloric acid (5ml)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b980ff7e83b445aa937853b8bcde5c48
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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