2-Methyl-4-nitroaniline → HCID 13325055, compound

HRID 436342Notes

Reaction equation

HRID 436342 reaction equation
[C:1]([C:6]1[CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]([OH:15])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19].P(Cl)(Cl)Cl>C1(C)C(C)=CC=CC=1>[C:1]([C:6]1[CH:14]=[C:10]([C:11]([NH:19][C:18]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:17]=2[CH3:16])=[O:13])[C:9]([OH:15])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 74412-Methyl-4-nitroanilineHCID 24387Phosphorus trichlorideHCID 2687425-tert-amylsalicylic acid

Product 1

HCID 13325055HCID 13325055, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 10.4 g of 5-tert-amylsalicylic acid and 7.6 g of 2-methyl-4-nitroaniline in 100 ml of xylene is heated at 70° C and to the mixture is added a solution of 2.6 g of phosphorus trichloride in 10 ml of xylene. The whole mixture is refluxed for two and a half 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 9.4 g of the title compound as pale yellow crystals, melting at 150°-151° C.

Workup

  1. temperatureThe whole mixture is refluxed for two and a half 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-d50b71e33c6a4b27a4aea1b073c2c676
Source dataset
uspto-grants-1977_02
Patent number
US04008274

Reaction notes

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