Sodium Hydroxide → 7-amino-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

HRID 1686894

反応式

HRID 1686894 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[N:12]O)[CH2:7][CH2:6][CH2:5]2.[OH-:14].[Na+].CO.C(Cl)Cl>O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:14])[NH:12][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 766439426-Amino-3,4-dihydro-2H-naphthalen-1-one oxime

生成物 1

HCID 598623477-amino-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

6-Amino-3,4-dihydro-2H-naphthalen-1-one oxime (1.80 g, 10.2 mmol) and polyphosphoric acid (30 ml) were mixed together. The viscous mixture was heated to 100° C. with vigorous stirring as the mixture became homogeneous. After cooling to room temperature, the mixture was diluted with water (30 ml). 15% aqueous sodium hydroxide was added until the mixture became basic. Extraction with ethyl acetate (50 ml), drying over anhydrous magnesium sulfate, and concentration yielded a brown oil. Preparative TLC (5% MeOH/CH2Cl2) afforded 7-Amino-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (Bioorganic & Medicinal Chem. Lett., 2003, 13 4197) as a light brown oil, 21 mg. 1H NMR (400 MHz, DMSO-d6) δ 7.53 (s, 1H), 7.14-7.22 (m, 1H), 6.42-6.47 (m, 1H), 6.33 (s, 1H), 5.44 (s, 2H), 2.87-2.93 (m, 2H), 2.53-2.60 (m, 2H), 1.78-1.87 (m, 2H); MS (m/e) 177 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionExtraction with ethyl acetate (50 ml)
  3. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  4. customyielded a brown oil

出典と根拠

ORDレコード
ord-878cbd4f1e0d4cd8ba60720ea2819e06
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

関連ノート

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