m-Toluidine → Ethyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylate

HRID 486435Notes

Reaction equation

HRID 486435 reaction equation
O=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3]1.[CH3:12][C:13]1[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[CH3:12][C:13]1[CH:14]=[C:15]([NH:19][CH:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3]2)[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 7934m-ToluidineHCID 8030ThiopheneHCID 277754Ethyl 3-oxopyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15124798Ethyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 7.9 parts of ethyl 3-oxo-1-pyrrolidinecarboxylate, 5.35 parts of 3-methylbenzenamine, 1 part of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 12.4 parts (100%) of ethyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylate as a residue (intermediate 19).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0aca31dae9a94893ba63a9f693f61341
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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