(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 970677Notes

Reaction equation

HRID 970677 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-fe3ad3924de449f4a5ccb0009841f9ea
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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