Sulfuric Acid → HCID 59410042, compound

HRID 1805133Notes

Reaction equation

HRID 1805133 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.[N+:21]([O-])([O-:23])=[O:22].[K+]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:21]([O-:23])=[O:22])=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 108458381-(2-(tert-butyl)phenyl)pyrrolidine

Product 1

HCID 59410042HCID 59410042, compoundYield 76.1%

Conditions

Temperature
0 °C

Procedure

1-(2-tert-butylphenyl)pyrrolidine (350 mg, 1.72 mmol) was added portionwise to conc. H2SO4 (1 mL) to generate a yellow homogeneous solution. The solution was then cooled to 0° C. and KNO3 (191 mg, 1.9 mmol) was added portionwise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice-water and extracted with DCM, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to obtain 1-(2-tert-butyl-5-nitrophenyl)pyrrolidine (325 mg, 76%). LC/MS: m/z 248.9 (M+H)+ at 2.39 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperaturemaintaining the internal temperature below 5° C
  2. additionpoured on ice-water
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-161962f1838c43e3a076525b465629e7
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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