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

HRID 220778

반응식

HRID 220778 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-241a1209b347432fbfe0d168bba0df6d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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