3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 396179Notes

Reaction equation

HRID 396179 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Cl:19][C:20]1[CH:21]=[C:22]([NH2:27])[CH:23]=[CH:24][C:25]=1[F:26]>CC(O)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 108940424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An amount of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile (7.1 g, 26.9 mmol), and 3-chloro-4-fluoro-phenylamine (3.9 g, 26.8 mmol), were stirred in 2-propanol (70 mL), and heated at reflux for 2 hours. The mixture was cooled to room temperature and stirred for an additional 20 hours. The reaction mixture was evaporated to dryness, stirred with ethyl acetate and saturated sodium bicarbonate solution. After separation of the layers, the organic layer was washed with saturated brine solution and dried on magnesium sulfate, to give a dark green powder (9.9 g, 99%), which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture was evaporated to dryness
  4. stirringstirred with ethyl acetate and saturated sodium bicarbonate solution
  5. customAfter separation of the layers
  6. washthe organic layer was washed with saturated brine solution
  7. customdried on magnesium sulfate

Sources & evidence

ORD record
ord-02b0de6ba631466580d08addf87b88f4
Source dataset
uspto-grants-2003_08
Patent number
US06608048B2

Reaction notes

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