6,6-Dimethyl-2-nitro-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine → 6,6-Dimethyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amine

HRID 407748Notes

Reaction equation

HRID 407748 reaction equation
[CH3:1][C:2]1([CH3:14])[O:7][CH2:6][C:5]2=[CH:8][C:9]([N+:11]([O-])=O)=[N:10][N:4]2[CH2:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:14])[O:7][CH2:6][C:5]2=[CH:8][C:9]([NH2:11])=[N:10][N:4]2[CH2:3]1

Participants

4

Reactant 1

HCID 866840186,6-Dimethyl-2-nitro-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine

Product 1

HCID 866840196,6-Dimethyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask was purged with nitrogen and charged with 139c (0.21 g, 1.25 mmol), 10% palladium on carbon (50% wet, 125 mg), and methanol (10 mL). The mixture was evacuated, charged with hydrogen gas, and stirred at room temperature for 2 h. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 139d (167 mg, 93%). MS-ESI: [M+H]+ 168.1

Workup

  1. customA 50-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d4795e9c0d94638ad1760387e07c6e7
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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