Water → Ethyl 1-(3-bromophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1294358Notes

Reaction equation

HRID 1294358 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[NH:5][CH:6]=[C:7]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1Cl)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[C:15]3[C:14](=[CH:19][CH:18]=[CH:17][N:16]=3)[C:13](=[O:21])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6]2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471910HCID 178471910, compound

Product 1

HCID 11057804Ethyl 1-(3-bromophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The crude compound from Step 1 was dissolved in tetrahydrofuran (0.3 M), the solution was cooled to 0° C., and sodium hydride (as a 60% dispersion in oil, 1.3 eq) was added in portions. After stirring at 0° C. for 1 hour, the mixture was allowed to warm up to room temperature. After 2 hours, water was added to the suspension and and the insoluble solid was filtered and washed copiously with water. When dry, the solid was stirred in ether at room temperature for 24 hours and filtered to afford the title compound as a cream-colored solid.

Workup

  1. temperatureto warm up to room temperature
  2. waitAfter 2 hours
  3. filtrationthe insoluble solid was filtered
  4. washwashed copiously with water
  5. customWhen dry
  6. stirringthe solid was stirred in ether at room temperature for 24 hours
  7. filtrationfiltered

Sources & evidence

ORD record
ord-57caa9857e8341c3a7d8f459e2e78e7b
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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