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

HRID 589076Notes

Reaction equation

HRID 589076 reaction equation
[N+:1]([C:4]1[C:9]2[NH:10][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)([C:14]([NH2:16])=[O:15])[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:9]2[NH:10][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)([C:14]([NH2:16])=[O:15])[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 904099005-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 904089895-amino-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide (0.040 g, 0.13 mmol) was dissolved in methanol (5 mL) in a Parr bottle and degassed with nitrogen, followed by addition of palladium (10% on carbon) (20 mg, 0.2 mmol). The reaction vessel was charged to 50 PSI with hydrogen and shaken for 2 h. The reaction mixture was then filtered and concentrated to give crude 5-amino-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide as a glass (0.040 g. 100%). LCMS calculated for C14H15N4O2 (M+H)+: m/z=271.1. found: 271.1.

Workup

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

Sources & evidence

ORD record
ord-52323459db484e56b7b551ea98531087
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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