Levulinic Acid → 1-(3'-Amino-4',6'-dimethylphenyl)-5-methyl-pyrrolidin-2-one

HRID 1706605

Reaction equation

HRID 1706605 reaction equation
[H][H].[C:3]([OH:10])(=O)[CH2:4][CH2:5][C:6]([CH3:8])=O.[NH2:11][C:12]1[CH:13]=[C:14]([C:16]([CH3:20])=[CH:17][C:18]=1[CH3:19])[NH2:15]>C(O)C.[Pt]=O>[NH2:11][C:12]1[CH:13]=[C:14]([N:15]2[CH:6]([CH3:8])[CH2:5][CH2:4][C:3]2=[O:10])[C:16]([CH3:20])=[CH:17][C:18]=1[CH3:19]

Participants

6

Reactant 3

HCID 11579Levulinic AcidHCID 8543864,6-Diamino-1,3-m-xyleneHCID 178418361HCID 178418361, compound

Product 1

HCID 128332741-(3'-Amino-4',6'-dimethylphenyl)-5-methyl-pyrrolidin-2-oneYield 80%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 0.2 g of platinum oxide in 25 ml of ethanol is treated with hydrogen and a solution of 34.8 g (0.3 mol) of levulinic acid and 85 g (0.62 mol) of 3-amino-4,6-dimethylaniline in 300 ml of ethanol is then added. The hydrogenation is carried out at room temperature. The desired pyrrolidinone derivative is obtained in a yield of about 80%.

Workup

  1. customis carried out at room temperature

Sources & evidence

ORD record
ord-f747abcd37754d728da8effe14acd0fa
Source dataset
uspto-grants-1980_06
Patent number
US04208202

Linked notes

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