2-(2,6-Dimethyl-3-nitrophenyl)-1,3-dioxolane → 2-(3-Amino-2,6-dimethylphenyl)-1,3-dioxolane

HRID 619686Notes

Reaction equation

HRID 619686 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]1[O:16][CH2:15][CH2:14][O:13]1>C(OCC)(=O)C.[Pt]=O>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([CH:12]2[O:13][CH2:14][CH2:15][O:16]2)[C:4]([CH3:11])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 218470332-(2,6-Dimethyl-3-nitrophenyl)-1,3-dioxolane

Product 1

HCID 218470392-(3-Amino-2,6-dimethylphenyl)-1,3-dioxolaneYield 100.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.7 g of 2-(2,6-dimethyl-3-nitrophenyl)-1,3-dioxolane in 30 ml of ethyl acetate was hydrogenated in the presence of 0.2 g of platinum oxide for 45 minutes. The catalyst was filtered off and the solution was concentrated to a crystalline residue. Recrystallization from hexane yielded 2.35 g of 2-(3-amino-2,6-dimethylphenyl)-1,3-dioxolane, m.p. 100-103° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solution was concentrated to a crystalline residue
  3. customRecrystallization from hexane

Sources & evidence

ORD record
ord-2144cbffdd4549fb976991804cbf151a
Source dataset
uspto-grants-1999_09
Patent number
US05959113

Reaction notes

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