Ammonium Hydroxide → 4-Quinolinamine, 8-fluoro-N-(2-(4-phenyl-2-thiazolyl)ethyl)-

HRID 487124

Reaction equation

HRID 487124 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.Cl.[NH2:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1.[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:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 27365874-Chloro-8-fluoroquinolineHCID 161929212-(4-Phenyl-thiazol-2-yl)-ethylamine hydrochloride

Product 1

HCID 1987224-Quinolinamine, 8-fluoro-N-(2-(4-phenyl-2-thiazolyl)ethyl)-Yield 21.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.0 g of 4-chloro-8-fluoroquinoline was added 2.6 g of 2-β-aminoethyl-4-phenylthiazole monohydrochloride. The mixture was stirred under nitrogen and heated to 170°-175° C. for one hour. The mixture was then cooled and 250 mL of a 50:50 mixture of ammonium hydroxide and water was added. The product was extracted into CH2Cl2, which was then concentrated to dryness. Recrystallizing from pentane/CH2Cl2 gave 0.410 g of the title product. Yield 21.6%. M.P. 134°-135° C.

Workup

  1. temperatureheated to 170°-175° C. for one hour
  2. temperatureThe mixture was then cooled
  3. additionwas added
  4. extractionThe product was extracted into CH2Cl2, which
  5. concentrationwas then concentrated to dryness
  6. customRecrystallizing from pentane/CH2Cl2

Sources & evidence

ORD record
ord-7cdc42133eb64af7826d7baafe0a8044
Source dataset
uspto-grants-1994_03
Patent number
US05294622

Linked notes

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