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

HRID 618255

Reaction equation

HRID 618255 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-0f86b88d69c74c7798a463364e738130
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Linked notes

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