Acetic Acid → HCID 20311331, compound

HRID 2420231Notes

Reaction equation

HRID 2420231 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:5]=1[NH:6][CH2:7][CH:8](C)C#N)([O-:3])=[O:2].OS(O)(=O)=O.[C:23]([O-:26])([O-])=[O:24].[Na+].[Na+].[C:29](O)(=O)C>O>[CH3:29][C:7]([NH:6][C:5]1[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:8])[C:23]([OH:26])=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 12417477HCID 12417477, compound

Product 1

HCID 20311331HCID 20311331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

47 g (mol/5 ) of 2-nitro-4-methoxy-(2'-methyl-2'-cyanoethyl)-aniline, 36 ml of H2O, 36 ml of acetic acid and 36 ml of H2SO4 are heated under reflux for 25 minutes. The reaction mixture is poured into iced water and is made alkaline with an Na2CO3 solution. 4.5 G of solid are eliminated by filtration. The solution is washed first of all with ethyl acetate and then acidified. The formed crystals are water extracted. Yield: 23.8 g = 47.7% (theoretical yield = 50.8 g) of a deep red solid of melting point 119°-121° C. After recrystallisation (ethylacetate plus decoloring carbon) a red solid, m.p. = 124°-126° C. is obtained.

Workup

  1. temperatureunder reflux for 25 minutes
  2. filtration4.5 G of solid are eliminated by filtration
  3. washThe solution is washed first of all with ethyl acetate
  4. extractionextracted
  5. customAfter recrystallisation (ethylacetate plus decoloring carbon) a red solid
  6. customm.p. = 124°-126° C. is obtained

Sources & evidence

ORD record
ord-15ec259ec5654fe685537103fbb6248c
Source dataset
uspto-grants-1978_08
Patent number
US04110337

Reaction notes

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