Sodium Hydroxide → 1,2,3,4-Tetrahydro-benzo(b)azepin-5-one

HRID 220778

反応式

HRID 220778 の反応式
C1(C)C=CC(S([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)(=O)=O)=CC=1.[OH-].[Na+]>>[NH:10]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]1=2

参加物

3

反応物 2

HCID 14798Sodium HydroxideHCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

生成物 1

HCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-one収率 79%

反応条件

温度
100 °C

実験手順

Polyphosphoric acid (25 g) was heated at 100° C. under nitrogen until it could be stirred. 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one from Example E5.4 (2.6 g, 8.26 mmol) was added portionwise and the reaction mixture was heated at 100° C. for 1.5 h. It was poured into ice and basified with 2M NaOH(aq). The aqueous layer was extracted twice with dichloromethane. The organic extracts were combined, washed with brine, dried and reduced in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (1.05 g, 79%).

後処理

  1. additionIt was poured into ice
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washwashed with brine
  4. customdried
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

出典と根拠

ORDレコード
ord-241a1209b347432fbfe0d168bba0df6d
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

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