Sarcosine → 4-Methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 623189Notes

Reaction equation

HRID 623189 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[NH:11]([CH2:13][C:14](O)=[O:15])[CH3:12].C(N(CC)CC)C>CS(C)=O>[CH3:12][N:11]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[NH:8][C:14](=[O:15])[CH2:13]1

Participants

5

Reactant 3

HCID 1088SarcosineHCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 129386634-Methyl-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.2 g of o-fluoro-nitrobenzene, 3.2 g of sarcosine and 5.2 ml triethylamine was stirred in 25 ml DMSO at 70° C. for 4 days. The mixture was then evaporated in vacuo and the residue was partitioned between water and methylene chloride. The organic phase was evaporated in vacuo. The residue was dissolved in 100 ml 96% ethanol and was hydrogenated at normal pressure using 0.5 g Pd/C. After completion of hydrogen uptake, the mixture was filtered and evaporated in vacuo. The residue was washed with water with disodium carbonate, ether and water. Yield of title compound: 1.3 g M.p. 132° C.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customthe residue was partitioned between water and methylene chloride
  3. customThe organic phase was evaporated in vacuo
  4. dissolutionThe residue was dissolved in 100 ml 96% ethanol
  5. filtrationAfter completion of hydrogen uptake, the mixture was filtered
  6. customevaporated in vacuo
  7. washThe residue was washed with water with disodium carbonate, ether and water

Sources & evidence

ORD record
ord-841ed395d116492ebcf5483b358d251f
Source dataset
uspto-grants-1988_09
Patent number
US04774245

Reaction notes

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