2,3-Dimethyl-5,6-dinitro-1,4-dimethoxybenzene → 2,3-Dimethyl-5,6-diamino-1,4-dimethoxybenzene

HRID 1278722Notes

Reaction equation

HRID 1278722 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([N+:11]([O-])=O)=[C:4]([N+:14]([O-])=O)[C:3]=1[O:17][CH3:18]>CCO.[Pd]>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([NH2:11])=[C:4]([NH2:14])[C:3]=1[O:17][CH3:18]

Participants

4

Reactant 1

HCID 154576882,3-Dimethyl-5,6-dinitro-1,4-dimethoxybenzene

Product 1

HCID 184311722,3-Dimethyl-5,6-diamino-1,4-dimethoxybenzeneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,3-Dimethyl-5,6-dinitro-1,4-dimethoxybenzene (4.0 g; 15 mmol) in EtOH (120 mL) was heated to solution, and 10% palladium on charcoal (1.0 g) was added.. The reaction mixture was hydrogenated at 45 psig for 3 hours. After work-up, 2.41 g (83% yield) of 2,3-dimethyl-5,6-diamino-1,4-dimethoxybenzene was obtained as a yellow solid, m.p. 107-110° C.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-f5712891209943f0adac19aee4dd3d4a
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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