2-Methyl-4-nitroaniline → 5-Tert-butyl-2'-methyl-4'-nitrosalicylanilide

HRID 436341Notes

Reaction equation

HRID 436341 reaction equation
[C:1]([C:5]1[CH:13]=[C:9]([C:10]([OH:12])=O)[C:8]([OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:17]=1[NH2:18].P(Cl)(Cl)Cl>C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[CH:13]=[C:9]([C:10]([NH:18][C:17]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:16]=2[CH3:15])=[O:12])[C:8]([OH:14])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 74412-Methyl-4-nitroanilineHCID 24387Phosphorus trichlorideHCID 852815-(1,1-Dimethylethyl)salicylic acid

Product 1

HCID 130256755-Tert-butyl-2'-methyl-4'-nitrosalicylanilideYield 70.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of 9.7 g of 5-tert-butylsalicylic acid and 7.6 g of 2-methyl-4-nitroaniline in 120 ml of xylene is heated at 65° to 70° C. To a reaction solution is added a solution of 2.6 g of phosphorus trichloride in 30 ml of xylene. The whole mixture is refluxed for 2 hours. The hot reaction solution is decanted. The supernatant solution is cooled on an ice bath. The crystalline precipitate is collected by filtration. Recrystallization from methanol gives 11.5 g of the title compound as pale yellow needles, melting at 202°-204° C.

Workup

  1. temperatureThe whole mixture is refluxed for 2 hours
  2. customThe hot reaction solution is decanted
  3. temperatureThe supernatant solution is cooled on an ice bath
  4. filtrationThe crystalline precipitate is collected by filtration
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-7aa4c1fba5fb4159b7299f81cd956eac
Source dataset
uspto-grants-1977_02
Patent number
US04008274

Reaction notes

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