3,4-Dichloroaniline → HCID 22466657, compound

HRID 612247Notes

Reaction equation

HRID 612247 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Cl:25])[NH2:21]>C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466657HCID 22466657, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4chloro-6-nitro-3quinolinecarbonitrile, 250 ml ethanol, and 4.17 g (25.6 mmol) 3,4-dichloroaniline was heated to reflux under N2. At 3.5 hours, removed head and made basic with saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solids and washed with water. Dissolved in ethyl acetate, stirred with Darco, filtered, stripped solvent and dried in vacuo, giving 2.106 g of yellow solid: mass spectrum (electrospray m/e): M+H=359.1, 361.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved head
  4. customazeotroped with ethanol
  5. customSlurried residue with hexane, collected solids
  6. washwashed with water
  7. dissolutionDissolved in ethyl acetate
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-545249f7d5914d378d3c6ac5fb4b9156
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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