Ethyl bromoacetate → HCID 54474405, compound

HRID 441231Notes

Reaction equation

HRID 441231 reaction equation
[OH:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.[H-].[Na+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C)C=O>[CH2:32]([O:31][C:29]([CH2:28][O:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1)=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 73885489HCID 73885489, compound

Product 1

HCID 54474405HCID 54474405, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-hydroxyimino-1-(4-nitrobenzoyl) -2,3,4,5-tetrahydro-1H-1-benzazepine (500 mg) in N,N-dimethylformamide (10 ml) was treated with sodium hydride (72 mg, 60% w/w in mineral oil) at 0° C. The reaction mixture was stirred at 0° C. for 5 minutes and then at ambient temperature for 30 minutes. Ethyl bromoacetate (301 mg) was added, and the reaction mixture was stirred for 2 hours. The reaction was quenched with aqueous hydrochloric acid and the mixture was diluted with ethyl acetate. The organic phase was washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, and brine. The organic solution was dried over magnesium sulfate and concentrated to give crude 5-ethoxycarbonylmethoxyimino-1-(4-nitrobenzoyl) -2,3,4,5-tetrahydro-1H-1-benzazepine. This product was taken on without further purification (700 mg).

Workup

  1. waitat ambient temperature for 30 minutes
  2. stirringthe reaction mixture was stirred for 2 hours
  3. customThe reaction was quenched with aqueous hydrochloric acid
  4. additionthe mixture was diluted with ethyl acetate
  5. washThe organic phase was washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, and brine
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb48260ce6e347fba375cf8476e61083
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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