Tetrahydrofuran → 4-amino-N,N,2-trimethylbenzamide

HRID 469825Notes

Reaction equation

HRID 469825 reaction equation
[CH3:1][C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C1COCC1>CO.[Pd]>[NH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([N:6]([CH3:8])[CH3:7])=[O:5])=[C:2]([CH3:1])[CH:12]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 62604610N,N,2-trimethyl-4-nitrobenzamide

Product 1

HCID 536229124-amino-N,N,2-trimethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.7 g (8.16 mmol) 2,N,N-trimethyl-4-nitro-benzamide in 45 ml MeOH:THF=1:1 is hydrogenated in the presence of 0.2 g 10% Pd/C (Fluka 75990). The reaction mixture is filtered (2 glass fiber filters used) and the filtrate is concentrated in vacuo to afford the crude title compound.

Workup

  1. filtrationThe reaction mixture is filtered (2 glass fiber filters used)
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-8cd8849841184a608b42eb6ad4f7817e
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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