N-t-butyloxycarbonyl-3,5-dinitro-4-methylaniline → 4-Amino-2,6-Dinitrotoluene

HRID 1106763

Reaction equation

HRID 1106763 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]([CH3:18])=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH3:18][C:12]1[C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]([NH2:8])=[CH:10][C:11]=1[N+:19]([O-:21])=[O:20]

Participants

3

Reactant 1

HCID 18789671N-t-butyloxycarbonyl-3,5-dinitro-4-methylaniline

Product 1

HCID 295744-Amino-2,6-DinitrotolueneYield 47.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-t-butyloxycarbonyl-3,5-dinitro-4-methylaniline (7.8 g, from above) and trifluoroacetic acid (100 mL) was stirred at room temperature for 15 min. After evaporation of the solvent under reduced pressure, the residue was taken up in ethyl acetate (100 mL), washed with saturated sodium bicarbonate solution, half-saturated sodium chloride solution, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by flash column chromatography on silica gel eluting with acetone:hexane (1:3) to give 4-methyl-3,5-dinitro-phenylamine (2.45 g).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. washwashed with saturated sodium bicarbonate solution, half-saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by flash column chromatography on silica gel eluting with acetone:hexane (1:3)

Sources & evidence

ORD record
ord-b79fbd14030f44eba97c12f2ec4f6a0f
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Linked notes

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