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

HRID 2353860Notes

Reaction equation

HRID 2353860 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 85.3%

Procedure

To preheated polyphosphoric acid (PPA, 220 g) at 70-80° C. was added 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (50.0 g, 0.16 mol). The mixture was stirred for 3.0 h at the same temperature and then poured into ice water. After the pH was adjusted to about 8-9 by adding aq NaOH, the mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (eluent, 3:1 n-hexanes:ethyl acetate) to give 1,2,3,4-Tetrahydro-benzo[b]azepin-5-one (22 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent, 3:1 n-hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-735e315f7dc94e65b4dee01f413b5500
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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