HCID 10737082, compound → HCID 178432042, compound

HRID 1197768Notes

Reaction equation

HRID 1197768 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:24]([O-])=O)=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=3[O-:22])[C:9]=2[CH:23]=1)(=O)[CH3:2]>C(O)(=O)C.[C].[Pd]>[CH3:2][C:1]1[NH:24][C:6]2[CH:7]=[C:8]3[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=4[O-:22])[C:9]3=[CH:23][C:5]=2[N:4]=1

Participants

4

Reactant 1

HCID 10737082HCID 10737082, compound

Product 1

HCID 178432042HCID 178432042, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 500 mg 2-(6-acetamido-3,4dihydro-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-4-yl)pyridine 1-oxide in 10 ml acetic acid, was added 40 mg 10% palladium-carbon to perform catalytic hydrogenation, the reaction mixture was filtered by the use of Celite, and the filtrate was stirred at 100° C. for 30 minutes. After cooling, the solvent was distilled off under reduced pressure, the rest was neutralized by addition of a saturated aqueous solution of sodium bicarbonate and extracted with chloroform, the extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off from the dried solution under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (elutant: 1:1 mixture of chloroform and methanol), and further recrystallized from ethanol-isopropyl ether, thus giving 180 mg of 2-(7,8-dihydro-2,6,6-trimethyl-6H-[1,4]oxazino[2,3-f]benzimidazol-8-yl)pyridine 1-oxide.

Workup

  1. filtrationthe reaction mixture was filtered by the use of Celite
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionthe rest was neutralized by addition of a saturated aqueous solution of sodium bicarbonate
  5. extractionextracted with chloroform
  6. washthe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off from the dried solution under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by column chromatography on silica gel (elutant: 1:1 mixture of chloroform and methanol)
  11. customfurther recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-ebecf2eb72f14ec5bc52339fea547c3f
Source dataset
uspto-grants-1994_01
Patent number
US05278158

Reaction notes

Loading…