3-Bromo-4-fluoroaniline → HCID 22466562, compound

HRID 612126Notes

Reaction equation

HRID 612126 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].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH2:21]>C(O)C>[Br: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[F:25]

Participants

4

Reactant 2

HCID 27792863-Bromo-4-fluoroanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466562HCID 22466562, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.8 g (16.33 mmol) of 4-chloro-6-nitro-3-quinolinecarbonitrile and 3.7 g (20 mmol) of 3-bromo-4-fluoroaniline in 200 mL of ethanol was refluxed for 3hr. After the solvent was removed, the residue as dissolved in ethyl acetate and washed with sodium bicarbonate. The product was collected as a pale yellow solid, 6.5 g (71%); ESMS m/z 387.3, 389.2, mp 269-270° C. (dec).

Workup

  1. temperaturewas refluxed for 3hr
  2. customAfter the solvent was removed
  3. dissolutionthe residue as dissolved in ethyl acetate
  4. washwashed with sodium bicarbonate
  5. customThe product was collected as a pale yellow solid, 6.5 g (71%)

Sources & evidence

ORD record
ord-fba7ddaad2894b22863c4df21d996b3d
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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