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

HRID 903876

Reaction equation

HRID 903876 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-59ca0f7c59a542658e4977b661a6f56f
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Linked notes

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