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

HRID 971088Notes

Reaction equation

HRID 971088 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 (500 mL), the solution was cooled to 0° C., and sodium hydride (as a 60% dispersion in oil, 9.4 g, 235 mmol) was added in portions. After stirring at 0° for 1 hour, the mixture was allowed to warm up to room temperature. After 2 hours, water (400 mL) 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 (150 mL) 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 (150 mL) at room temperature for 24 hours
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7d0f8a2a7338415caaf7a1a759537dfd
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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