Acetic Acid → HCID 10638836, compound

HRID 1197767Notes

Reaction equation

HRID 1197767 reaction equation
[NH2:1][C:2]1[C:3]([N+:21]([O-])=O)=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=3[O-:19])[C:6]=2[CH:20]=1.[C:24](O)(=[O:26])C>O.[C].[Pd]>[CH3:11][C:9]1([CH3:12])[O:10][C:5]2=[CH:4][C:3]3[NH:21][C:24](=[O:26])[NH:1][C:2]=3[CH:20]=[C:6]2[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=2[O-:19])[CH2:8]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10852879HCID 10852879, compound

Product 1

HCID 10638836HCID 10638836, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 632 mg 2-(6-amino-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine 1 -oxide in 10 ml acetic acid, was added 50 mg of 10% palladium carbon, and catalytic hydrogenation was performed. The reaction mixture was filtered by the use of Celite, the solvent was distilled off from the filtrate under reduced pressure, the residue was dissolved in 10 ml tetrahydrofuran, 5 ml tetrahydrofuran solution containing 324 mg carbonyldiimidazole was added under ice cooling, and the mixture was stirred overnight at room temperature. The precipitate which separated out was filtered off, the solvent was distilled off from the filtrate under reduced pressure, the residue thus obtained was dissolved in water, the aqueous solution was washed with chloroform and allowed to stand at room temperature for one hour, and the crystals which separated out were collected by filtration, thus giving 130 mg of 2-(7,8-dihydro-6,6-dimethyl-2-oxo-6H-[1,4]oxazino[2,3-f]benzimidazolin-8-yl)pyridine 1-oxide.

Workup

  1. filtrationThe reaction mixture was filtered by the use of Celite
  2. distillationthe solvent was distilled off from the filtrate under reduced pressure
  3. dissolutionthe residue was dissolved in 10 ml tetrahydrofuran
  4. addition5 ml tetrahydrofuran solution containing 324 mg carbonyldiimidazole
  5. additionwas added under ice cooling
  6. customThe precipitate which separated out
  7. filtrationwas filtered off
  8. distillationthe solvent was distilled off from the filtrate under reduced pressure
  9. customthe residue thus obtained
  10. washthe aqueous solution was washed with chloroform
  11. waitto stand at room temperature for one hour
  12. customthe crystals which separated out
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7051c2010f034e81832bbeda299e37d3
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

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