Ethyl Acetate → 4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile

HRID 1935185Notes

Reaction equation

HRID 1935185 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[F:28])[NH2:24].C(OCC)(=O)C>CCCCCC>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:25]=[CH:26][C:27]=1[F:28]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 97083-Chloro-4-fluoroanilineHCID 110113054-Chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 110581574-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrileYield 103.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile (26.8 g 96.5 mmol) and 3-chloro-4-fluoroaniline 14.05 g 96.5 mmol) in 900 ml of iso-propanaol were refluxed under N2 for 3.5 hrs. TLC (ethyl acetate: hexane=1:1) showed no starting material left. After standing at room temperature overnight, the hydrochloride salt was filtered off and washed with isopropanol and ether giving 4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile 38.6 g (95%) as a yellow hydrochloride salt.

Workup

  1. waitleft
  2. filtrationthe hydrochloride salt was filtered off
  3. washwashed with isopropanol and ether

Sources & evidence

ORD record
ord-a30cebc15ed040bb8468573e525c1c09
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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