2-Ethoxy-1-methoxy-4-nitro-benzene → 3-Ethoxy-4-methoxyaniline

HRID 1297103Notes

Reaction equation

HRID 1297103 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[NH2:10])[CH3:2]

Participants

4

Reactant 1

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzene

Product 1

HCID 167919473-Ethoxy-4-methoxyanilineYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Leave under hydrogen pressure (Patm) for 12 hours, 5 g of 2-ethoxy-1-methoxy-4-nitrobenzene (XIXaa), 500 mg of 10% palladium on charcoal (10% by weight of product to reduce), in 200 ml of methanol. Filter on celite, rinse several times with methanol. Evaporate to dryness. Take up in ether and evaporate. One obtains 3.28 g of the abovenamed product as a pinkish white powder. Yield: 79%. 1H-NMR (CDCl3, 300 MHz): d 1.46 (t, 3H, —CH3), 3.33 (s, 2H exchangeable, —NH2), 3.81 (s, 3H, OCH3), 4.05 (q, 2H, OCH2), 6.22(d, 1H Ar), 6.28 (dd, 1H Ar), 6.71 (d, 1H Ar).

Workup

  1. customLeave under hydrogen pressure (Patm) for 12 hours
  2. filtrationFilter on celite
  3. washrinse several times with methanol
  4. customEvaporate to dryness
  5. customevaporate

Sources & evidence

ORD record
ord-70d9dd3c7c714b6dad0ba048af450658
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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