Hydrochloric Acid → 3-[4-(3-Chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid

HRID 1582972Notes

Reaction equation

HRID 1582972 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([C:7]1[C:8]([NH:18][CH2:19][CH3:20])=[N:9][C:10]([CH:13]([O:16]C)OC)=[CH:11][CH:12]=1)=O.[H-].[Na+].Cl[CH:27]([CH2:33][CH2:34][C:35]([O-])=[O:36])[C:28]([O:30]CC)=[O:29].C[O-].[Na+].S(=O)(=O)(O)O.Cl>C(O)C.O1CCOCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[N:9][C:10]([CH:13]=[O:16])=[CH:11][CH:12]=3)[N:18]([CH2:19][CH3:20])[C:35](=[O:36])[C:34]=2[CH2:33][CH2:27][C:28]([OH:30])=[O:29])[CH:21]=[CH:22][CH:23]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 227166793-(3-Chlorobenzoyl)-2-ethylamino-6-dimethoxymethylpyridineHCID 22716689Monoethyl chloroglutarate

Product 1

HCID 227166593-[4-(3-Chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A DMF solution of 3-(3-chlorobenzoyl)-6-dimethoxymethyl-2-ethylaminopyridine was treated with sodium hydride at 0° C. and then monoethyl chloroglutarate was added thereto, followed by heating at 80° C. under stirring. Thereafter, the reaction mixture was worked up in a usual manner. The resulting compound was dissolved in ethanol and sodium methoxide was added thereto at 0° C., followed by heating under reflux for 1 hour. The reaction mixture was cooled to 0° C. and then concentrated sulfuric acid was added thereto, followed by heating under reflux for 1 hour. Thereafter, the reaction mixture was worked up in a usual manner. The resulting compound was dissolved in dioxane and 6M hydrochloric acid was added thereto at 0° C. and, after being warmed to room temperature, the whole was stirred for 3 hours. Thereafter, the reaction mixture was worked up in a usual manner to obtain 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid. NMR1: 10.12 (1H, s), 7.70 (1H, d, J=8.1 Hz), 1.44 (3H, t, J=6.9 Hz).

Workup

  1. customat 0° C.
  2. temperatureby heating
  3. temperatureunder reflux for 1 hour
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. temperatureby heating
  6. temperatureunder reflux for 1 hour
  7. temperatureat 0° C. and, after being warmed to room temperature
  8. stirringthe whole was stirred for 3 hours

Sources & evidence

ORD record
ord-4c4b13dea48f4fc98c7facc4d8415505
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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