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

HRID 220778

Reaction equation

HRID 220778 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-241a1209b347432fbfe0d168bba0df6d
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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