O-Methylhydroxylamine hydrochloride → 6-cyano-3,4-dihydro-4-(5-methoxyimino-1-cyclopenten-1-yl)-2,2-dimethyl-2H-1,4-benzoxazine

HRID 37118Notes

Reaction equation

HRID 37118 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][N:8]([C:14]3[C:18](=O)[CH2:17][CH2:16][CH:15]=3)[C:7]=2[CH:20]=1)#[N:2].Cl.[CH3:22][O:23][NH2:24]>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][N:8]([C:14]3[C:18](=[N:24][O:23][CH3:22])[CH2:17][CH2:16][CH:15]=3)[C:7]=2[CH:20]=1)#[N:2]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 107306176-cyano-3,4-dihydro-2,2-dimethyl-4-(5-oxo-1-cyclopenten-1-yl)-2H-1,4-benzoxazine

Product 1

HCID 539103166-cyano-3,4-dihydro-4-(5-methoxyimino-1-cyclopenten-1-yl)-2,2-dimethyl-2H-1,4-benzoxazineYield 78.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 3 ml of pyridine was dissolved 0.3 g of 6-cyano-3,4-dihydro-2,2-dimethyl-4-(5-oxo-1-cyclopenten-1-yl)-2H-1,4-benzoxazine followed by addition of 0.26 g of methoxyamine hydrochloride. The mixture was stirred at room temperature overnight and the solvent was then distilled off under reduced pressure. The residue was poured in water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled Off under reduced pressure. Finally the residue was washed with ethanol-ether to give 0.26 g of 6-cyano-3,4-dihydro-4-(5-methoxyimino-1-cyclopenten-1-yl)-2,2-dimethyl-2H-1,4-benzoxazine.

Workup

  1. distillationthe solvent was then distilled off under reduced pressure
  2. additionThe residue was poured in water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled Off under reduced pressure
  7. washFinally the residue was washed with ethanol-ether

Sources & evidence

ORD record
ord-ae7e2fa6f93645d18f2670d5ab1da1d7
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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