Sodium hydride → 1-(2-phthalimidoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

HRID 2163334

Reaction equation

HRID 2163334 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[H-].[Na+].Cl[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]>CN(C)C=O>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][N:7]2[C:8]3[C:3](=[C:2]([CH3:1])[CH:11]=[C:10]([CH3:12])[N:9]=3)[CH:4]=[CH:5][C:6]2=[O:13])[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 234274N-(2-Chloroethyl)phthalimideHCID 53744055,7-dimethyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 233354051-(2-phthalimidoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5,7-dimethyl-1,8-naphthyridin-2(1H)-one (3.5 g., 0.02 mole) in 25 ml. of dry dimethyl formamide under nitrogen atmosphere is added a 57% suspension of sodium hydride in mineral oil (0.84 g., 0.02 mole). This mixture is stirred at room temperature for 1/2 hour. A mixture of N-(2-chloroethyl) phthalimide (4.6 g., 0.022 mole) in 25 ml. of dry dimethylformamide is added to the first suspension. The mixture is stirred at steam bath temperature for 16 hours. On cooling, it is filtered to remove salt and the filtrate evaporated to dryness in vacuo to afford 1-(2-phthalimidoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one.

Workup

  1. stirringThe mixture is stirred at steam bath temperature for 16 hours
  2. temperatureOn cooling
  3. filtrationit is filtered
  4. customto remove salt
  5. customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-18d955581fb347dd96764e29e12a9fa4
Source dataset
uspto-grants-1979_01
Patent number
US04133885

Linked notes

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