Hydrochloric Acid → HCID 22716691, compound

HRID 1582989Notes

Reaction equation

HRID 1582989 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[CH2:22][CH2:23][CH2:24][OH:25])[CH:5]=[CH:6][CH:7]=1.[CH3:26]C(C)([O-])C.[Na+].CI.Cl>O.C(O)(C)(C)C>[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[CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 12991190HCID 12991190, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 22716691HCID 22716691, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a 10 ml tert-butanol solution containing 500 mg of 4-(3-chlorophenyl)-1-ethyl-3-(3-hydroxypropyl)-7-methyl-1,8-naphthyridin-2(1H)-one were added 300 mg of sodium tert-butoxide and 0.2 ml of methyl iodide successively, followed by stirring under heating at an oil bath temperature of 60° C. for 2 hours. After the reaction mixture was cooled to room temperature, water and 1M hydrochloric acid were added thereto, and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from diisopropyl ether to obtain 180 mg of 4-(3-chlorophenyl)-1-ethyl-3-(3-methoxypropyl)-7-methyl-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-94cd7c643d4f4178ac1052ee18df8a8b
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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