O-(o-Aminophenoxy)benzoic acid lactam → 10,11-Dihydrodibenzo(b,f)(1,4)oxazepine

HRID 1456928Notes

Reaction equation

HRID 1456928 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1[C:12]2[C:13](=O)[NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[O:17][C:11]=2[CH:10]=[CH:9][CH:8]=1>C(OCC)C>[CH:7]1[C:12]2[CH2:13][NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[O:17][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 72374O-(o-Aminophenoxy)benzoic acid lactamHCID 21226445Aluminium lithium hydride

Product 1

HCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineYield 96.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a dry 250 ml three-necked flask equipped with reflux condenser and thermometer, lithium aluminum hydride (1.8 g, 0.047 mol) was suspended in dry diethyl ether (75 ml) under a nitrogen atmosphere. Cautiously, 10,11-dihydrodibenz [b,f][1,4]oxazepin-11-one (5.0 g, 0.024 mol) was added in portions. The mixture was heated at reflux temperature for 5 hours, cooled to room temperature and left stirring overnight. The reaction mixture was quenched by cautious addition of water (1.8 ml), 4N sodium hydroxide (1.8 ml) and finally water (5.4 ml). Diethyl ether and toluene were added and the mixture was filtered. The filtercake was washed with diethyl ether, toluene and ethyl acetate, successively. The filtrate was evaporated until dryness, affording 4.55 g (96%) of 10,11-dihydrodibenz[b,f][1,4]oxazepine.

Workup

  1. customIn a dry 250 ml three-necked flask equipped
  2. temperaturewith reflux condenser
  3. temperatureThe mixture was heated
  4. temperatureat reflux temperature for 5 hours
  5. waitleft
  6. customThe reaction mixture was quenched by cautious addition of water (1.8 ml), 4N sodium hydroxide (1.8 ml) and finally water (5.4 ml)
  7. additionDiethyl ether and toluene were added
  8. filtrationthe mixture was filtered
  9. washThe filtercake was washed with diethyl ether, toluene and ethyl acetate
  10. customThe filtrate was evaporated until dryness

Sources & evidence

ORD record
ord-95459b407b4f47448a3b52ab4ace45a8
Source dataset
uspto-grants-1998_12
Patent number
US05846968

Reaction notes

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