Ethyl Acetate → 2-Methoxy-N1,N1-dimethyl-1,4-benzenediamine

HRID 417321Notes

Reaction equation

HRID 417321 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[N:6]([CH3:8])[CH3:7].[C:15](OCC)(=[O:17])C>[Pd]>[CH3:15][O:17][C:4]1[CH:3]=[C:11]([NH2:12])[CH:10]=[CH:9][C:5]=1[N:6]([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 52515483-methoxy-N,N-dimethyl-4-nitroaniline

Product 1

HCID 120168852-Methoxy-N1,N1-dimethyl-1,4-benzenediamineYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 3-methoxy-N,N-dimethyl-4-nitroaniline (Bionet) (0.5 g, 2.6 mmol) and Pd/C (Aldrich, 10%, 0.1 g) in ethyl acetate (10 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 0.5 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 2-methoxy-N,N-dimethyl-benzene-1,4-diamine as a dark brown oil (0.4 g, 94%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c5dbe8871b0f4035b21b143ac6e7a0fc
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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