Ammonium Hydroxide → 4-Quinolinamine, 8-fluoro-N-[2-(2-thienyl)ethyl]-

HRID 1196473Notes

Reaction equation

HRID 1196473 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][CH2:19][NH2:20].[OH-].[NH4+]>O>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:20][CH2:19][CH2:18][C:14]1[S:13][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 116521ThiopheneethanamineHCID 27365874-Chloro-8-fluoroquinoline

Product 1

HCID 1641834-Quinolinamine, 8-fluoro-N-[2-(2-thienyl)ethyl]-Yield 34.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of 4-chloro-8-fluoroquinoline and 2.8 g of 2-(2-thienyl)ethyl amine was heated under nitrogen to 160°-165° C. for two hours, then cooled and combined with 200 mL of a 50:50 mixture of ammonium hydroxide and water. The product was extracted into CH2Cl2, which was then concentrated to dryness. The residue was recrystallized from pentane/CH2Cl2 to give 1.0 g of the title product. Yield 34.5%. M.P. 157°-158° C.

Workup

  1. temperaturewas heated under nitrogen to 160°-165° C. for two hours
  2. temperaturecooled
  3. extractionThe product was extracted into CH2Cl2, which
  4. concentrationwas then concentrated to dryness
  5. customThe residue was recrystallized from pentane/CH2Cl2

Sources & evidence

ORD record
ord-72076ec467874e8ab94205392896fbe5
Source dataset
uspto-grants-1992_05
Patent number
US05114939

Reaction notes

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