Nitric Acid → 2,4-Dimethyl-5-nitroaniline

HRID 392082

Reaction equation

HRID 392082 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:13])[CH:7]=1>S(=O)(=O)(O)O>[N+:1]([C:11]1[CH:10]=[C:9]([NH2:12])[C:8]([CH3:13])=[CH:7][C:6]=1[CH3:5])([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 72502,4-Dimethylaniline

Product 1

HCID 2280072,4-Dimethyl-5-nitroanilineYield 71,117.898%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
15 °C

Procedure

Conc. nitric acid (33 g) was added dropwise over 3 h to a stirred solution of m-xylidine (40 g, 0.33 mmol) in conc. sulfuric acid (400 g) at <15° C. After complete addition the reaction was stirred at 15° C. for 1 h then poured onto ice (600 mL), stirred for 30 min and filtered The yellow filter-cake was neutralised with saturated aqueous sodium hydrogen carbonate solution (500 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (Magnesium sulfate), filtered and the solvent removed under vacuum to leave a crude solid. The solid was recrystalised (ethanol-water) to give the product as an orange solid (39 g, 71%, contains 20% di-nitro). IR νmax (Nujol)/cm−1 3469, 3386, 3239, 2956, 2925, 2855, 1719, 1636, 1514, 1461, 1377, 1339, 1297, 1273, 1222, 1170, 1034, 992, 885, 870, 849, 805, 758, 745, 723, 640, 607 and 571; NMR δH (400 MHz; CDCl3) 7.15 (1H, s), 6.87 (1H, s), 4.99 (2H, br. s), 2.21 (3H, s), 1.97(3H, s).

Workup

  1. additionAfter complete addition the reaction
  2. additionthen poured onto ice (600 mL)
  3. stirringstirred for 30 min
  4. filtrationfiltered The
  5. filtrationyellow filter-cake
  6. extractionextracted with ethyl acetate (3×200 mL)
  7. dry with materialThe combined organic extracts were dried (Magnesium sulfate)
  8. filtrationfiltered
  9. customthe solvent removed under vacuum
  10. customto leave a crude solid
  11. customThe solid was recrystalised (ethanol-water)

Sources & evidence

ORD record
ord-6149544d93134611b8fc9908990eacee
Source dataset
uspto-grants-2004_10
Patent number
US06800627B1

Linked notes

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