(7-nitro-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol → (7-amino-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol

HRID 2102975Notes

Reaction equation

HRID 2102975 reaction equation
[N+:1]([C:4]1[CH:13]=[N:12][C:11]2[NH:10][CH:9]([CH2:14][OH:15])[CH2:8][O:7][C:6]=2[CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[N:12][C:11]2[NH:10][CH:9]([CH2:14][OH:15])[CH2:8][O:7][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 68703685(7-nitro-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol

Product 1

HCID 59020667(7-amino-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanolYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 500 mL round bottom flask were combined (7-nitro-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol (0.320 g, 0.00152 mol), 10%-palladium on carbon (0.06 g, 0.0005 mol) and methanol (50 mL). The apparatus was evacuated, then hydrogen was introduced and the mixture was allowed to stir overnight (at 1 atm presuure). The mixture was then filtered through Celite® and the filtrate was concentrated under vacuum to yield an oil (0.252 g, 89%) which was used directly in the next step without further purification. (0.252 g, 89%) LC-MS 0.29 min. M/Z=181.9(M+1).

Workup

  1. customInto a 500 mL round bottom flask were combined
  2. customThe apparatus was evacuated
  3. additionhydrogen was introduced
  4. filtrationThe mixture was then filtered through Celite®
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-381cd6c5766d40529cf123333982bb1c
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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