Sodium Bicarbonate → 1-Amino-6,11-dihydrodibenz[b,e]oxepin-11-one

HRID 1827Notes

Reaction equation

HRID 1827 reaction equation
C([NH:4][C:5]1[C:15]2[C:14](=[O:16])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=O)C.C(=O)(O)[O-].[Na+]>Cl>[NH2:4][C:5]1[C:15]2[C:14](=[O:16])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 196930381-Acetamido-6,11-dihydrodibenz[b,e]oxepin-11-one

Product 1

HCID 196930241-Amino-6,11-dihydrodibenz[b,e]oxepin-11-oneYield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In concentrated hydrochloric acid (10 ml), 1-acetamido-6,11-dihydrodibenz[b,e]oxepin-11-one obtained in Reference Example 3(0.25 g, 0.94 mmol) was heated under reflux for 2 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate (25 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure to give 1-amino-6,11-dihydrodibenz[b,e]oxepin-11-one as a yellow solid (0.17 g, 81%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionfollowed by extraction with ethyl acetate (25 ml)
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cca8c52f7ba34625b95aa6d245498aa5
Source dataset
uspto-grants-1998_03
Patent number
US05726325

Reaction notes

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