Nitric Acid → 3-Nitro-4-(propan-2-yl)aniline

HRID 924667Notes

Reaction equation

HRID 924667 reaction equation
[CH3:1][CH:2]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:3].S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17]>>[N+:16]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:4]=1[CH:2]([CH3:3])[CH3:1])[NH2:8])([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 74644-Isopropylaniline

Product 1

HCID 221118273-Nitro-4-(propan-2-yl)anilineYield 71%

Conditions

Temperature
8 °C

Procedure

4-(Propan-2-yl)aniline (10.12 mL, 74 mmol) was added drop wise to sulfuric acid (96%, 57 mL), cooled to 8° C., maintaining the temperature below 10° C. After the addition, the reaction mixture was cooled to −5° C., before the addition of a mixture of nitric acid (100%, 3.7 mL) and sulfuric acid (96%, 9 mL), keeping the temperature below 0° C. The reaction mixture was then stirred at the same temperature for 1 h. The reaction mixture was poured into ice (200 mL) and the precipitate filtered and washed with water. The solid was suspended with water (100 mL) and neutralized with ammonium hydroxide (35%). The precipitate was filtered and dried in the oven to obtain a light-brown solid (9.49 g, 71%).

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. additionAfter the addition
  3. customthe temperature below 0° C
  4. filtrationthe precipitate filtered
  5. washwashed with water
  6. filtrationThe precipitate was filtered
  7. customdried in the oven

Sources & evidence

ORD record
ord-ad3a2789617842f9827bdf3f20777e83
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

Loading…