Potassium Bromide → 6,11-Dihydro-11-hydroxydibenz[b,e]oxepin-2-carboamide

HRID 1982373Notes

Reaction equation

HRID 1982373 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:3]1=2.[K+].[Br-]>>[OH:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:3]1=2

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 124468236,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboamide

Product 1

HCID 136495656,11-Dihydro-11-hydroxydibenz[b,e]oxepin-2-carboamide

Procedure

In a similar manner as above, 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboamide IX was prepared from the oxepin-carboamide VIII in a quantitative yield. Recrystallization from tetrahydrofuran gave pure crystals having a melting point of 257°-258° C. IR spectrum (KBr tablet, cm-1): 3350, 3180, 1665, 1625, 1410, 1255; NMR spectrum (CDCl3 +d6DMSO, δ-value, ppm): 5.10(d, 1H), 5.78, 5.85, 6.09 (each d, total 3H), 6.6-8.1(m, 9H).

Workup

  1. customRecrystallization from tetrahydrofuran
  2. customgave pure crystals

Sources & evidence

ORD record
ord-e16f27a12b4a4f4588b1d3cfc55fabf9
Source dataset
uspto-grants-1986_06
Patent number
US04596804

Reaction notes

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