2-(Methoxymethyl)-4-nitroaniline → 2-Methoxymethyl-p-phenylenediamine

HRID 625898Notes

Reaction equation

HRID 625898 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=1[NH2:6].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH2:3][C:4]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

5

Reactant 2

HCID 114011432-(Methoxymethyl)-4-nitroanilineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 97938592-Methoxymethyl-p-phenylenediamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a Parr hydrogenation bottle previously purged with argon, are placed a solution of 2-methoxymethyl-4-nitroaniline (5.0 g, 27.5 mmol) in ethyl acetate (50 mL) and 0.25 g of 10% palladium on carbon. The bottle is mounted on a Parr shaker and hydrogenation is carried out under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. The pressure is carefully monitored for hydrogen uptake and additional hydrogen is introduced to keep the pressure above 50 psig. The hydrogenation is carried out for 3.5 hours after which the catalyst is removed by vacuum filtration. The filtrate is concentrated to about 25 mL and toluene (25 mL) is added to precipitate the product, which is collected by vacuum filtration and dried at 60° C. under vacuum. The product yield is 4.5 g; 1H-NMR (500 MHz, DMSO-d6) δ 3.23 (s, 3 H), 4.11 (s, 2 H), 4.21 (s, 2 H), 4.24 (s, 2 H), 6.33 (dd, 1 H), 6.37 (d, 1 H), 6.41 (d, 1 H).

Workup

  1. customInto a Parr hydrogenation bottle previously purged with argon
  2. additionis introduced
  3. customafter which the catalyst is removed by vacuum filtration
  4. concentrationThe filtrate is concentrated to about 25 mL and toluene (25 mL)
  5. additionis added
  6. customto precipitate the product, which
  7. filtrationis collected by vacuum filtration
  8. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-53e68000b53245f1a04aa8119175c1dc
Source dataset
uspto-grants-2016_04
Patent number
US09309185B2

Reaction notes

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