1-Acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethane → 1-Acetoxy-2-[(3,4-methylenedioxy)-6-aminophenyl]ethane

HRID 990071Notes

Reaction equation

HRID 990071 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]2[O:16][CH2:17][O:18][C:9]=2[CH:8]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([NH2:13])=[CH:11][C:10]2[O:16][CH2:17][O:18][C:9]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 234454281-Acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethane

Product 1

HCID 234452401-Acetoxy-2-[(3,4-methylenedioxy)-6-aminophenyl]ethaneYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 1-acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethane (0.8 g, 3.13 mmol) in ethyl acetate (25 mL) was subjected to catalytic hydrogenation using 10% palladium on carbon (100 mg) at 50 psi for 30 min. The catalyst was filtered and the solvent was removed under reduced pressure to give 1 -acetoxy-2-[(3,4-methylenedioxy)-6-aminophenyl]ethane as a solid (0.69 g, 98% yield).

Workup

  1. customfor 30 min
  2. filtrationThe catalyst was filtered
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fc29ade318e24167a0d1bf16d5489806
Source dataset
uspto-grants-2002_10
Patent number
US06458805B2

Reaction notes

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