Sodium hydride → HCID 23335402, compound

HRID 903875Notes

Reaction equation

HRID 903875 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:15])[NH:8]2)[CH3:2].[H-].[Na+].Cl.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22]Cl>CN(C)C=O>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][N:8]1[C:9]2[C:4](=[C:3]([CH2:1][CH3:2])[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=2)[CH:5]=[CH:6][C:7]1=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 23335385HCID 23335385, compound

Product 1

HCID 23335402HCID 23335402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5,7-diethyl-1,8-naphthyridin-2(1H)-one (4.04 g., 0.02 mole) in 25 ml. of dry dimethylformamide 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 0.5 hours. Then a mixture of 2-dimethylaminoethyl chloride hydrochloride (3.17 g., 0.022 mole) and a 57% suspension of sodium hydride in mineral oil (0.93 g., 0.022 mole) in 25 ml. of dry dimethylformamide is added to the above suspension. The mixture is stirred at steam bath temperature overnight (16 hours). After the mixture is cooled to room temperature it is filtered to remove salt (2.6 g., theory 2.45 g.). Removal of the solvent under reduced pressure gives a pale tan waxy solid (4.8 g.). Several recrystallizations from hexane gives 1-(2-dimethylaminoethyl)-5,7-diethyl-1,8-naphthyridin-2(1H)-one melting at 59.5°-61° C.

Workup

  1. stirringThe mixture is stirred at steam bath temperature overnight (16 hours)
  2. temperatureAfter the mixture is cooled to room temperature it
  3. filtrationis filtered
  4. customto remove salt (2.6 g., theory 2.45 g.)
  5. customRemoval of the solvent under reduced pressure
  6. customgives a pale tan waxy solid (4.8 g.)
  7. customSeveral recrystallizations from hexane

Sources & evidence

ORD record
ord-c52bc3fdb06c453b8398fb53e96eb809
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

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