Ethanol → HCID 12988027, compound

HRID 1582980Notes

Reaction equation

HRID 1582980 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([C:15]2[C:24]3[C:19](=[N:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]([CH2:26][CH3:27])[C:17](=[O:28])[C:16]=2C(O)=O)[CH:12]=[CH:13][CH:14]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])=CC=1.C([N:51]([CH2:54]C)CC)C.[CH2:56]([OH:58])[CH3:57]>O>[Cl:8][C:9]1[CH:10]=[C:11]([C:15]2[C:24]3[C:19](=[N:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]([CH2:26][CH3:27])[C:17](=[O:28])[C:16]=2[NH:51][C:54](=[O:39])[O:58][CH2:56][CH3:57])[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22716713HCID 22716713, compound

Product 1

HCID 12988027HCID 12988027, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 10 ml toluene solution containing 1.00 g of 4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-carboxylic acid were added 900 mg of DPPA and 0.5 ml of triethylamine, followed by heating at an oil bath temperature of 100° C. for 1 hour. Then, 10 ml of ethanol was added thereto and the whole was further stirred under heating for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (toluene-ethyl acetate) and then recrystallized from ethyl acetate to obtain 590 mg of ethyl N-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]carbamate as colorless crystals.

Workup

  1. temperatureunder heating for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by a silica gel column chromatography (toluene-ethyl acetate)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-93258c598cbb46758e7bdf8b28f3f3cb
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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