Water → HCID 18472450、化合物

HRID 566122ノート

反応式

HRID 566122 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 18472651tert-butyl 4-(4-bromo-2-formyl-N-methylanilino)butyrateHCID 178418922HCID 178418922、化合物

生成物 2

HCID 184722637-bromo-1-methyl-2,3-dihydro-1H-1-benzoazepine-4-carboxylic acid収率 17%HCID 18472450HCID 18472450、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f3e66335d8cb49acb961fd4efe2cf5ed
出典データセット
uspto-grants-2001_01
特許番号
US06172061B2

反応ノート

読み込み中…