Ethanol → 10,11-Dihydrodibenzo(b,f)(1,4)oxazepine

HRID 718090Notes

Reaction equation

HRID 718090 reaction equation
[CH:1]1[C:6]2[C:7](=O)[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.B.C(O)C>C1COCC1>[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6331BoraneHCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Product 1

HCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dibenzo[b,f][1,4]oxazepin-11(10H)-one (1.001 g, 4.7 mmol) was dissolved in THF (20 mL) and the borane (2M in THF, 20 mL, 40.0 mmol) was added. The reaction mixture was refluxed for 3 hours. The mixture was cooled down to room temperature and an excess of ethanol was added to quench the reaction. The resulting mixture was refluxed for 2 hours. The mixture was cooled down and concentrated in vacuo. The residue was dissolved in ethyl acetate and the organic layer was washed with water and brine, dried over sodium sulfate, filtered and evaporated to afford title compound 398 (0.945 g, quantitative). MS (m/z): 198.1 (M+H). 1H NMR (CD3OD) δ (ppm): 7.29-7.19 (m, 2H), 7.16-7.04 (m, 2H), 7.01-6.99 (m, 1H), 6.82-6.78 (m, 1H), 6.63-6.59 (m, 2H), 4.88 (s, 1H), 4.39 (s, 2H). MS (m/z): 198.1 (M+H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customto quench
  3. customthe reaction
  4. temperatureThe resulting mixture was refluxed for 2 hours
  5. temperatureThe mixture was cooled down
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washthe organic layer was washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-6c872bd1a2d4474e95de9b5e2627a6bc
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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