Nitric Acid → 2-Amino-2-methyl-1-(4-nitrophenyl)propane sulfate
Reaction equation
Cl.[NH2:2][C:3]([CH3:12])([CH3:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N+:13]([O-])([OH:15])=[O:14].[OH:17][S:18]([OH:21])(=[O:20])=[O:19]>>[S:18]([OH:21])([OH:20])(=[O:19])=[O:17].[NH2:2][C:3]([CH3:12])([CH3:11])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1Participants
Procedure
A slight modification in the procedure described previously [Lavin et al, J. Biol. Chem., Vol. 256, p. 11944 (1981)] enables direct isolation of the product instead of column chromatographic separation of ortho (20%) and para (80%) isomers, both of which are products of the nitration. 2-Amino-2-methyl-1-phenylpropane hydrochloride (97 g, 0.41 mol) was dissolved in concentrated H2SO4 (195 ml) and the solution was cooled in an ice bath. Nitric acid (70%, 40 ml, 56 g, 0.6 mol) was added with stirring while the temperature was kept under 10° C. and then the solution was stirred for an additional 20 min. Next the mixture was poured on ice (4 l), and after 16 h white crystals were filtered, washed with cold water and methanol, and dried in air. Yield: 71.3 g (56%); mp 293°-298° C. dec; Rf 0.24 (dichloro-methane-methanol-ammonia, 4:1:0.03).
Workup
- custominstead of column chromatographic separation of ortho (20%) and para (80%) isomers
- temperaturethe solution was cooled in an ice bath
- customwas kept under 10° C.
- stirringthe solution was stirred for an additional 20 min
- additionNext the mixture was poured on ice (4 l)
- filtrationafter 16 h white crystals were filtered
- washwashed with cold water and methanol
- customdried in air
Sources & evidence
- ORD record
- ord-b6e7f763d18d49288b053ad017f60e0b
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04894219
Reaction notes
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