1-Fluoro-2-nitrobenzene → 1,2,3,3a-Tetrahydropyrrolo[1,2-a]quinoxalin-4(5h)-one

HRID 623184Notes

Reaction equation

HRID 623184 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[NH:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O>CS(C)=O.C(O)C.[Pd]>[O:15]=[C:13]1[NH:8][C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:11]2[CH2:18][CH2:17][CH2:16][CH:12]12

Participants

6

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 145742L-Proline

Product 1

HCID 31279171,2,3,3a-Tetrahydropyrrolo[1,2-a]quinoxalin-4(5h)-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

1.5 ml of o-fluoro-nitrobenzene and 8.2 g of L-proline were stirred at 60° C. for 3 hours in 50 ml DMSO. The mixture was then evaporated in vacuo to give a yellow oil. This oil was dissolved in 250 ml 96% ethanol and was hydrogenated at normal pressure at room temperature using 2 g 5% Pd/C as catalyst. After completion of hydrogen uptake, the mixture was filtered and evaporated in vacuo to give the title compound. M.p. 169°-172° C.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customto give a yellow oil
  3. customwas hydrogenated at normal pressure at room temperature
  4. filtrationAfter completion of hydrogen uptake, the mixture was filtered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-05afaea056e24087a662af406caa673b
Source dataset
uspto-grants-1988_09
Patent number
US04774245

Reaction notes

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