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

HRID 482770Notes

Reaction equation

HRID 482770 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 (5 ml), 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 (5 ml)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d59d552b153e4fda92a71510b85cf9fe
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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