p-Toluidine → 2-Chloro-3-(4-methylanilino)naphthalene-1,4-dione

HRID 1895500

Reaction equation

HRID 1895500 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:11](=[O:22])[C:12]2[C:17]([C:18](=[O:21])[C:19]=1[Cl:20])=[CH:16][CH:15]=[CH:14][CH:13]=2>C(O)C>[Cl:20][C:19]1[C:18](=[O:21])[C:17]2[C:12]([C:11](=[O:22])[C:10]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 8342Dichlone

Product 1

HCID 2658672-Chloro-3-(4-methylanilino)naphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Toluidin (1.4 g, 13.2 mmol) was added to the solution of 2,3-dichloro-1,4-naphthoquinone (1.0 g, 4.4 mmol) in ethanol (300 ml). The reaction mixture was allowed to stir at room temperature for over night. The precipitated product was filtered off and washed with cold ethanol. The product was purified by recrystallization with ethanol/CHCl3 (1:5) to afford the fine reddish needles. Yield: 0.642 g (53.8%), Mp: 295° C.

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with cold ethanol
  3. customThe product was purified by recrystallization with ethanol/CHCl3 (1:5)
  4. customto afford the fine reddish needles

Sources & evidence

ORD record
ord-7228c457586d490a86004de5e007d223
Source dataset
uspto-grants-2013_08
Patent number
US08513437B2

Linked notes

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