Sulfuric Acid → 2-Tert-butyl-5-nitroaniline
Reaction equation
OS(O)(=O)=O.[C:6]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])([CH3:9])([CH3:8])[CH3:7].[N+:17]([O-])([O-:19])=[O:18].[K+].BrC1N=CC=CC=1C(N)=O>O>[C:6]([C:10]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=1[NH2:12])([CH3:9])([CH3:7])[CH3:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To H2SO4 (98%, 389 mL) in a 500 mL 3-neck flask was added 2-tert-butyl aniline (40.6 mL). The reaction was cooled to −10° C. and KNO3 in 3.89 g aliquots was added every 6 min for a total of 10 aliquots. Tried to maintain temperature at −5° C. to −10° C. After final addition of KNO3, stirred the reaction for five min then it was poured onto ice (50 g). The black mix was diluted with H2O and extracted with EtOAc. The aqueous layer was basified with solid NaOH slowly then extracted with EtOAc (2×). The combined organic layers were washed with 6N NaOH and then with a mix of 6N NaOH and brine, dried over Na2SO4, filtered and concentrated in vacuo to obtain crude 2-tert-butyl-5-nitro-aniline as a dark red-black oil which solidified when standing at RT. The crude material was triturated with about 130 mL hexanes. After decanting the hexanes, the material was dried to obtain a dark-red black solid.
Workup
- temperatureTried to maintain temperature at −5° C. to −10° C
- customthe reaction for five min
- additionit was poured onto ice (50 g)
- additionThe black mix
- extractionextracted with EtOAc
- extractionextracted with EtOAc (2×)
- washThe combined organic layers were washed with 6N NaOH
- additionwith a mix of 6N NaOH and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a350655571c24bc38bae786d41339d9c
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507748B2
Reaction notes
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