HCID 12988027, compound → HCID 12988028, compound

HRID 1582981Notes

Reaction equation

HRID 1582981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[NH:22]C(=O)OCC)[CH:5]=[CH:6][CH:7]=1>C(O)C.O>[NH2:22][C:9]1[C:10](=[O:21])[N:11]([CH2:19][CH3:20])[C:12]2[C:17]([C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2

Participants

4

Reactant 1

HCID 12988027HCID 12988027, compound

Product 1

HCID 12988028HCID 12988028, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 720 mg portion of ethyl N-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]carbamate was stirred in 40 ml of an ethanol-3M sodium hydroxide aqueous solution (1:1) under heating at an oil bath temperature of 100° C. for 4 hours. After cooling to room temperature, the reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated brine and the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (toluene-ethyl acetate) and then recrystallized from diisopropyl ether-ethyl acetate to obtain 298 mg of 3-amino-4-(3-chlorophenyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by a silica gel column chromatography (toluene-ethyl acetate)
  6. customrecrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-e5007139015e4fbbb332ea1ad38b84d3
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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