N-methyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide → 5-amino-N-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide

HRID 589066Notes

Reaction equation

HRID 589066 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[NH:10][C:9]2[C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)=[O:4].[H][H]>CO.[Pd]>[NH2:15][C:11]1[C:9]2[NH:10][C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][O:7][C:8]=2[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 90409054N-methyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 904090745-amino-N-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Methyl-5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide (25 mg, 0.080 mmol) was dissolved in methanol (5 mL) in a Parr bottle and degassed with nitrogen, followed by addition of palladium (10% on carbon) (5 mg, 0.05 mmol). The reaction vessel was charged to 50 PSI hydrogen and shaken for 2 h. The reaction mixture was filtered and concentrated in vacuo to give crude 5-amino-N-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide (0.005 g. 100%). LCMS calculated for C15H17N4O2 (M+H)+: m/z=285.1. found: 285.0.

Workup

  1. customdegassed with nitrogen
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b216ea7eb2c14398b699d4f9df054a40
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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