Water → HCID 18472450, 화합물

HRID 566122노트

반응식

HRID 566122 반응식
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH2:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:7])=[C:4]([CH:20]=O)[CH:3]=1.C(O[K])(C)(C)C.O>C(O)(C)(C)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:7])[CH2:8][CH2:9][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:20][C:4]=2[CH:3]=1.[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:7])[CH2:8][CH2:9][C:10]([C:11]([OH:13])=[O:12])=[CH:20][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 18472651tert-butyl 4-(4-bromo-2-formyl-N-methylanilino)butyrateHCID 178418922HCID 178418922, 화합물

생성물 2

HCID 184722637-bromo-1-methyl-2,3-dihydro-1H-1-benzoazepine-4-carboxylic acid수율 17%HCID 18472450HCID 18472450, 화합물수율 77%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

In tert-butanol (250 ml) was dissolved tert-butyl 4-(4-bromo-2-formyl-N-methylanilino)butyrate (4.54 g) and tert-butoxy potassium (1.43 g), and the mixture was refluxed for 1 hour and cooled. To the mixture was added water (500 ml), and the mixture was extracted with ethyl acetate (500 ml×2). The aqueous layer was made weakly acidic with 1N hydrochloric acid (about 12.5 ml), and the mixture was extracted with ethyl acetate (500 ml). Both of these organic layer was washed with saturated brine (250 ml) and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (200 g, hexane:ethyl acetate=10:1→1:1) to give tert-butyl 7-bromo-1-methyl-2,3-dihydro-1-benzoazepine-4-carboxylate (3.33 g, 77%) and 7-bromo-1-methyl-2,3-dihydro-1H-1-benzoazepine-4-carboxylic acid (0.60 g, 17%).

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate (500 ml×2)
  4. extractionthe mixture was extracted with ethyl acetate (500 ml)
  5. washBoth of these organic layer was washed with saturated brine (250 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (200 g, hexane:ethyl acetate=10:1→1:1)

출처 및 근거

ORD 기록
ord-f3e66335d8cb49acb961fd4efe2cf5ed
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

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