Sulfuric Acid → HCID 22279241, compound

HRID 1805112Notes

Reaction equation

HRID 1805112 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[N+:19]([O-])([O-:21])=[O:20].[K+].[OH-].[Na+]>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:11])=[CH:12][C:13]=2[N+:19]([O-:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 807644-Cyclohexylbenzenamine

Product 1

HCID 22279241HCID 22279241, compoundYield 921%

Conditions

Temperature
0 °C

Procedure

4-cyclohexylaniline (15 g, 85.58 mmol) was added portionwise to conc. sulfuric acid (85 mL, 1.6 mol) to generate a homogeneous solution. The solution was then cooled to 0° C. and KNO3 (13 g, 128.6 mmol) was added portionwise maintaining the internal temperature below 5° C. The reaction was stirred for 5 minutes at −10° C. and then poured on ice water, basified with 6N NaOH solution and the aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and concentrated to obtain 4-cyclohexyl-3-nitroaniline (17 g, 921%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, J=8.5 Hz, 1H), 6.97 (d, J=2.5 Hz, 1H), 6.82 (dd, J=8.4, 2.5 Hz, 1H), 2.85 (ddd, J=11.4, 8.3, 3.2 Hz, 1H), 1.89-1.69 (m, 6H), 1.49-1.29 (m, 4H).

Workup

  1. temperaturemaintaining the internal temperature below 5° C
  2. additionpoured on ice water
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-74b122a0d7c64fa99ab7011a9036f962
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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