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

HRID 1376222Notes

Reaction equation

HRID 1376222 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-c9ee0a21897f43edbe67f8e2e9b15280
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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