N-bromobutanimide → Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate

HRID 906188Notes

Reaction equation

HRID 906188 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])#[N:2].[Br:19]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:19][C:12]1[CH:13]=[C:3]([C:1]#[N:2])[C:4]([NH:14][CH2:15][CH:16]([CH3:17])[CH3:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67405767Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate

Product 1

HCID 67402604Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 1.60 mmol) in DMF (10 mL) was added N-bromsuccinimide (284 mg, 1.60 mmol). The mixture was stirred overnight at 45° C. then cooled to room temperature and diluted with water then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to give ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate (374 mg, 72.0%) as a yellow solid. MS (EI) for C14H17BrN2O2: 324 (M+).

Workup

  1. temperaturethen cooled to room temperature
  2. extractionthen extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2309d0b922894f58a51278575f48ce06
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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