Ammonia → 4-Amino-1-methyl-3-nitro-1,8-naphthyridin-2(1H)-one

HRID 2244810Notes

Reaction equation

HRID 2244810 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[N+:14]([O-:16])=[O:15].[NH3:17]>C1COCC1>[NH2:17][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 714223334-Chloro-1-methyl-3-nitro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 451232974-Amino-1-methyl-3-nitro-1,8-naphthyridin-2(1H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4-chloro-1-methyl-3-nitro-1H-[1,8]naphthyridin-2-one (1.54 g, 6.43 mmol) (J. Med. Chem. 1992, 35, 2863-2870) in 40 mL of THF was treated with 7.2 mL of 28% aqueous ammonia (6.4 g, 51 mmol). After stirring at 20° C. 17 h, the solvent was evaporated under reduced pressure and water was added to the residue. The resulting precipitate was filtered and washed with water to give to give 4-amino-1-methyl-3-nitro-1H-[1,8]naphthyridin-2-one (1.35 g, 96% yield). 1H-NMR (DMSO): δ 8.74 (m, 2H), 8.35 (s, 2H), 7.38 (dd, 1H, J=8.0, 4.8 Hz), 3.58 (s, 3H).

Workup

  1. custom17 h, the solvent was evaporated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customto give

Sources & evidence

ORD record
ord-f30ae14c4f7a4a518bae9a85934bd6c1
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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