N-methyl-2-pyrrolidone → HCID 13749921, compound

HRID 542523Notes

Reaction equation

HRID 542523 reaction equation
Br[C:2]1[N:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[CH3:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.CN1CCCC1=O>O>[CH3:12][C:10]1[CH:9]=[C:8]2[C:3]([CH:4]=[CH:5][C:6](=[O:13])[NH:7]2)=[C:2]([N:18]2[CH:19]=[C:15]([CH3:14])[N:16]=[CH:17]2)[N:11]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 13749920HCID 13749920, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 13749921HCID 13749921, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture containing 9.56 g of 5-bromo-7-methyl-1,6-naphthyridin-2(1H)-one, 8.2 g of 4-methyl-1H-imidazole and 22 ml of N-methylpyrrolidin-one was heated with stirring in an oil bath at 140° C. for 20 hours. The reaction mixture containing some separated solid was diluted with about 150 ml of water and the solid was collected, triturated with water, washed with ethanol and dried to give 6.0 g of 7-methyl-5-(4-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. 307°-308° C.

Workup

  1. temperaturewas heated
  2. additionThe reaction mixture containing some separated solid
  3. customthe solid was collected
  4. customtriturated with water
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-03c3bcb84e1f409aafbaad26714acaf9
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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