2-Methyl-4-nitroaniline → 2-Chloro-6-methyl-4-nitroaniline

HRID 1793662Notes

Reaction equation

HRID 1793662 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:12]OC(C)(C)C>C1(C)C=CC=CC=1.O>[Cl:12][C:5]1[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=[C:2]([CH3:1])[C:3]=1[NH2:4]

Participants

5

Reactant 2

HCID 74412-Methyl-4-nitroanilineHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 27334602-Chloro-6-methyl-4-nitroanilineYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-methyl-4-nitroaniline (56.0 g, 0.368 mol) was dispersed in toluene (430 ml) in a 1 liter four-neck flask. Tertiary butyl hypochloride (46.0 g, 0.423 mol) was added dropwise thereto, while cooled in iced water and stirred. The mixture was stirred at room temperature for 3 hours. The solids were filtered and washed three times with 200 ml of a 50% aqueous ethanol three times. They were then dried at 40° C. at a reduced pressure to obtain 55.33 g of a yellow solid (production yield 80%). The yellow solid was used in the subsequent step without purification.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. filtrationThe solids were filtered
  3. washwashed three times with 200 ml of a 50% aqueous ethanol three times
  4. customThey were then dried at 40° C. at a reduced pressure

Sources & evidence

ORD record
ord-c55acf361bef4b1091052b3ba3b0acef
Source dataset
uspto-grants-2006_07
Patent number
US07081548B2

Reaction notes

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