Water → HCID 14639189, compound

HRID 1460145Notes

Reaction equation

HRID 1460145 reaction equation
[C:1]1([C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10](=[O:17])[N:9]3[CH2:18][CH2:19][NH:20][C:8]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23]I.O>CN(C)C=O>[CH3:23][N:20]1[C:8]2[N:9]([C:10](=[O:17])[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14639175HCID 14639175, compound

Product 1

HCID 14639189HCID 14639189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

Dissolve 2,3-dihydro-10-phenyl-imidazo-[1,2-g][1,6]naphthyridin-5(1H)-one (2.63 g) in N,N-dimethylformamide (100 ml), and add the solution to a stirred suspension of dimethylformamide (25 ml) and sodium hydride (as a 60% dispersion in mineral oil). Use 0.25 g of the dispersion, and stir the resulting mixture for 1 hour at 25° C. Add methyl iodide (8.5 g), and stir for 15 hours, again at 25° C. Pour the mixture over ice and water (500 g), and extract with dichloromethane. Combine extracts, wash them with water and brine, dry them over magnesium or sodium sulfate, and concentrate them. Crystallize the residue from chloroform-acetone to obtain 2,3-dihydro-1-methyl-10-phenylimidazo[1,2-g]-[1,6]naphthyridin-5(1H)-one, mp 237°-240° C.

Workup

  1. additionadd the solution
  2. extractionextract with dichloromethane
  3. washCombine extracts, wash them with water and brine
  4. dry with materialdry them over magnesium or sodium sulfate
  5. concentrationconcentrate them
  6. customCrystallize the residue from chloroform-acetone

Sources & evidence

ORD record
ord-c546455c86d0484fb0c6166983445b48
Source dataset
uspto-grants-1991_12
Patent number
US05070086

Reaction notes

Loading…