Hydroxyamine hydrochloride → HCID 73867443, compound

HRID 1088799Notes

Reaction equation

HRID 1088799 reaction equation
[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12](=O)[CH2:13][CH2:14][N:3]1[C:4]=23.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C.O>[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12](=[N:17][OH:18])[CH2:13][CH2:14][N:3]1[C:4]=23

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 146857275,6-Dihydro-1H,3H,7H-[1,3]oxazino[5,4,3-ij]quinoline-3,7-dione

Product 1

HCID 73867443HCID 73867443, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

6,7-Dihydro-3,7-dioxo-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (5 g), hydroxylamine hydrochloride (2.1 g) and sodium acetate (7.5 g) were dissolved in a mixed solvent of ethanol-water (5:1) (90 ml) and the mixture was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off and the resulting residue was poured into water. Crystals which precipitated were collected by filtration and dried to give 6,7-dihydro-3-oxo-7-hydroxyimino-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine. The compound was dissolved in acetic acid (150 ml) and platinum oxide (250 mg) was added thereto. The mixture was subjected to catalytic reduction at 50° C. and 4 atmospheres. After completion of the catalytic reduction, catalyst was filtered off and the filtrate was concentrated to give 6,7-dihydro-3-oxo-7-amino-1H,3H,5H-pyrido [3,2,1-ij][3,1]benzoxazine (5 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionthe resulting residue was poured into water
  5. customCrystals which precipitated
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-473411a1fc2f4cb3b8044329dc83bde5
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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