Water → HCID 22329219, compound

HRID 587048Notes

Reaction equation

HRID 587048 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([N:6]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])[CH2:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:4]([CH:24]=O)[CH:3]=1.CC(C)([O-])C.[K+].O>C1(C)C=CC=CC=1.CC(O)(C)C>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])[CH2:7][CH2:8][C:9]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:24][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22328906HCID 22328906, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22329219HCID 22329219, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

In toluene (4.8 ml)/2-methyl-2-propanol (0.48 ml) was dissolved tert-butyl 4-[4-bromo(2-ethoxyethyl)-2-formylanilino]butyrate (2.4 g). To the solution was added potassium tert-butoxide. (72 mg), the mixture was stirred at 100° C. for 1 hour and cooled to room temperature. The reaction solution was added to water, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=6/1) to give tert-butyl 7-bromo-1-(2-ethoxyethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.15 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-e2a9c8d1dce84b74b30b7fb0a149effc
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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