4-Methoxy-N-methyl-2-nitrobenzenamine → 4-methoxy-1-N-methylbenzene-1,2-diamine

HRID 230001Notes

Reaction equation

HRID 230001 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N+:11]([O-])=O>CO.[Pd]>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH2:11]

Participants

4

Reactant 1

HCID 35543134-Methoxy-N-methyl-2-nitrobenzenamine

Product 1

HCID 45184444-methoxy-1-N-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound of Example 14 Step A (3 mmol, 547 mg) and 10% Pd—C (ca. 50 mg) were stirred in 10 mL of MeOH under H2 (balloon). After 3 h the solution was nearly colorless. The reaction mixture was filtered over celite and filter cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure affording a slightly orange solid. HPLC A: 0.44 min.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. filtrationfilter cake
  3. washwas washed with MeOH
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. customaffording a slightly orange solid
  6. custom0.44 min.

Sources & evidence

ORD record
ord-6b7c19260fe04da2939a8905fe3ca78f
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…