1-Chloro-2,4-dinitronaphthalene → 1-(3-Chloro-4-trifluoromethoxyphenylamino)-2,4-dinitronaphthalene

HRID 847734Notes

Reaction equation

HRID 847734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11])[NH2:5].Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([N+:25]([O-:27])=[O:26])=[CH:17][C:16]=1[N+:28]([O-:30])=[O:29].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([N+:25]([O-:27])=[O:26])=[CH:17][C:16]=2[N+:28]([O-:30])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 169871-Chloro-2,4-dinitronaphthaleneHCID 516892Sodium BicarbonateHCID 27738433-Chloro-4-(trifluoromethoxy)aniline

Product 1

HCID 205672681-(3-Chloro-4-trifluoromethoxyphenylamino)-2,4-dinitronaphthaleneYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 12.7 g (60 mmols) of 3-chloro-4-trifluoromethoxyaniline and 15.15 g (60 mmols) of 1-chloro-2,4-dinitronaphthalene in 150 ml of water was heated to the boil. 5.6 g (67 mmols) of sodium bicarbonate were introduced in the course of 30 minutes and heating was continued for 2 hours under reflux. After the mixture had cooled to 20° C., the product was filtered off. 24 g of 1-(3-chloro-4-trifluoromethoxyphenylamino)-2,4-dinitronaphthalene of melting point 140° C. were obtained; after recrystallization from ethanol, 17.4 g of melting point 159° C. were obtained.

Workup

  1. temperaturewas heated to the boil
  2. temperatureheating
  3. temperatureunder reflux
  4. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-a4fc12bdc2634e4d877d5cc71d7347ca
Source dataset
uspto-grants-1981_10
Patent number
US04293566

Reaction notes

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