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

HRID 379138Notes

Reaction equation

HRID 379138 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-quinoline-3-carbonitrile and 3.7 g (20 mmol) of 3-bromo-4-fluoroaniline in 200 mL of ethanol was refluxed for 3 hr. 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 3 hr
  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-2be731cea865414288a9ffb2db1c6c7c
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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