6,9-Dimethyl-3-nitro-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one → 3-Amino-6,9-dimethyl-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one

HRID 1078556Notes

Reaction equation

HRID 1078556 reaction equation
[N+:1]([C:4]1[CH:21]=[N:20][C:7]2[O:8][C:9]3[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:10]=3[N:11]([CH3:14])[C:12](=[O:13])[C:6]=2[CH:5]=1)([O-])=O>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:21]=[N:20][C:7]2[O:8][C:9]3[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:10]=3[N:11]([CH3:14])[C:12](=[O:13])[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 4539736,9-Dimethyl-3-nitro-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one

Product 1

HCID 4539743-Amino-6,9-dimethyl-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 3-nitro-6,9-dimethylpyrido[2,3-b][1,5]benzoxazepin-5(6H)-one (1.6 g, 5.6 mmol) in acetic acid (30 ml) was added a solution of stannous chloride dihydrate (10 g, 44 mmol) in conc. hydrochloric acid (13 ml). After stirring the mixture for 3 hours, the precipitated product was filtered and washed with ether. The product was then dissolved in water, basified with 2N sodium hydroxide, extracted with ether and ethyl acetate, dried (anhydrous magnesium sulfate), and concentrated. Crystallization from ethanol/hexane provided 0.82 g (57% of theory) of pure product as tan needles, m.p. 191°-193° C.

Workup

  1. filtrationthe precipitated product was filtered
  2. washwashed with ether
  3. dissolutionThe product was then dissolved in water
  4. extractionextracted with ether and ethyl acetate
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. concentrationconcentrated
  7. customCrystallization from ethanol/hexane
  8. customprovided 0.82 g (57% of theory) of pure product as tan needles, m.p. 191°-193° C.

Sources & evidence

ORD record
ord-e2034538e96849ce80313389cfb0d6af
Source dataset
uspto-grants-1996_08
Patent number
US05550122

Reaction notes

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