Stannous Chloride → 8-amino-5H-benzo[b][1,4]benzoxazepin-6-one

HRID 895974Notes

Reaction equation

HRID 895974 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[NH:10][C:9](=[O:18])[C:8]=2[CH:19]=1)([O-])=O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[NH:10][C:9](=[O:18])[C:8]=2[CH:19]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 6206222-Nitrodibenzo[b,f][1,4]oxazepin-11(10H)-one

Product 1

HCID 27563998-amino-5H-benzo[b][1,4]benzoxazepin-6-oneYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-nitro-10H-dibenzo[b,f][1,4]oxazepin-11-one (Example 3, 2.0 g, 7.8 mmol) and SnCl2 in 50 mL of denatured ethanol (85% ethanol, 15% wood alcohol) was stirred under reflux for 1 hr. The solvent was evaporated and the solid residue was washed with 200 mL of ethyl acetate. The ethyl acetate layer was washed with 1.0 N sodium hydroxide (2×100 mL)and water (2×100 mL), then dried over magnesium sulfate, filtered and evaporated to give an off white solid (yield 0.92 g, 52.3%).

Workup

  1. temperatureunder reflux for 1 hr
  2. customThe solvent was evaporated
  3. washthe solid residue was washed with 200 mL of ethyl acetate
  4. washThe ethyl acetate layer was washed with 1.0 N sodium hydroxide (2×100 mL)and water (2×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-23b3e0ea17c14b7c89183e7e12e88c74
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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