3,4-Dichloroaniline → HCID 22466657, compound

HRID 1935156Notes

Reaction equation

HRID 1935156 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) 4-chloro-6-nitro-3-quinolinecarbonitrile, 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-2b73d150f66a4d3bb1cc689c9e4e8a88
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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