Dimethyl nitroterephthalate → Dimethyl aminoterephthalate

HRID 2081763Notes

Reaction equation

HRID 2081763 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O>CO.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 21364Dimethyl nitroterephthalate

Product 1

HCID 79336Dimethyl aminoterephthalate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

23.9 g (0.1 mol) of dimethyl 2-nitroterephthalate are hydrogenated in a mixture of 100 ml of methanol and 200 ml of tetrahydrofuran with palladium/charcoal at 5 bar and 20° C. After the catalyst has been removed by suction filtering the solvent is evaporated off and the residue is recrystallised from methanol. Yield 18-19 g, yellowish crystals m.p. 130-131° C.

Workup

  1. customAfter the catalyst has been removed by suction
  2. filtrationfiltering the solvent
  3. customis evaporated off
  4. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-a4b49dd19940446aba34630355c2554b
Source dataset
uspto-grants-1993_02
Patent number
US05185442

Reaction notes

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