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

HRID 1918398Notes

Reaction equation

HRID 1918398 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH2:11][O:12][CH3:13])[CH:5]=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[CH3:13][O:12][CH2:11][C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][C:7]=1[NH2:10]

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

5 g (27.5 mmol) of 4-Nitro-2-methoxymethyl-aminobenzene and 0.250 g of palladium (10% on carbon) are placed in a 250 ml Parr bottle and 50 g of ethyl acetate is added. Hydrogenation is carried out using a Parr apparatus under 50-60 psig (64.7-74.7 psi or 446-515 kPa) of hydrogen pressure. In the course of the reaction the yellowish grey suspension turns to a darker grey suspension. The reaction is also carefully monitored for rapid hydrogen uptake and additional hydrogen is introduced to keep pressure above 50 psig (64.7 psi or 446 kPa). After 1 hour the suspension clears, leaving a yellow solution. The reaction is continued for 2.5 hours to ensure complete conversion. The catalyst is removed by filtration through glass microfiber filter paper. The filtrate is concentrated to ca. 25 ml, and 25 ml of toluene are added to precipitate the product. The product is collected on filter paper with suction and dried at 60° C. under vacuum. The product yield is 4.5 g.

Workup

  1. additionis added
  2. customIn the course of the reaction the yellowish grey suspension
  3. additionis introduced
  4. customleaving a yellow solution
  5. waitThe reaction is continued for 2.5 hours
  6. customThe catalyst is removed by filtration through glass microfiber
  7. filtrationfilter paper
  8. concentrationThe filtrate is concentrated to ca. 25 ml, and 25 ml of toluene
  9. additionare added
  10. customto precipitate the product
  11. customThe product is collected
  12. filtrationon filter paper with suction
  13. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-6b61a0bd8b1a47938f264807fd6b6079
Source dataset
uspto-grants-2013_12
Patent number
US08618326B2

Reaction notes

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