1-(6,7-dichloro-8-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone → 1-(8-Amino-2,3-dihydro-1,4-benzodioxin-5-yl)ethan-1-one

HRID 963361Notes

Reaction equation

HRID 963361 reaction equation
Cl[C:2]1[C:3]([N+:16]([O-])=O)=[C:4]2[O:15][CH2:14][CH2:13][O:12][C:5]2=[C:6]([C:9](=[O:11])[CH3:10])[C:7]=1Cl>[Pd].[OH-].[Na+].C(O)C>[NH2:16][C:3]1[CH:2]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[C:5]2[O:12][CH2:13][CH2:14][O:15][C:4]=12

Participants

5

Reactant 1

HCID 27636871-(6,7-dichloro-8-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)-1-ethanone

Product 1

HCID 232692381-(8-Amino-2,3-dihydro-1,4-benzodioxin-5-yl)ethan-1-oneYield 66.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5',6'-dichloro-2',3'-ethylenedioxy-4'-nitroacetophenone (2 g, 7.63 mmol) and 10% palladium on carbon (800 mg) in 17 mL of 15% sodium hydroxide and 160 mL of ethanol hydrogenated at 57 psi for 7 hours. The mixture was filtered and concentrated by rotary evaporation and the residue was stirred into water. Drying gave 4'-amino-2',3'-ethylenedioxyacetophenone (970 mg, 5.04 mmol), m.p. 135°-136° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by rotary evaporation
  3. customDrying

Sources & evidence

ORD record
ord-32e24568503d413da55befb84f4a1dcc
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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