Ammonia → HCID 19017551, compound

HRID 1728319Notes

Reaction equation

HRID 1728319 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.[F:13][C:14]([F:32])([F:31])[C:15]1[N:20]=[C:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH2:30])=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.N>ClCCl>[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:30][CH2:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:14]([F:32])([F:13])[F:31])[N:20]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 27365874-Chloro-8-fluoroquinolineHCID 19017555HCID 19017555, compound

Product 1

HCID 19017551HCID 19017551, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-8-fluoroquinoline (1.81 g, 0.01 mol), and 2-(4-(6-trifluoromethyl-2-pyridinyloxy)-phenyl)ethylamine (2.82 g, 0.01 mol), triethylamine (1.1 g, 0.011 mol) was heated at 180°-190° C. for two hours and allowed to cool to a glass. Dichloromethane (50 mL) and concentrated ammonia solution (50 mL) were added, and the mixture was stirred until the glass dissolved. The organic phase was washed with 0.5M sodium hydroxide solution and water, and was dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallization from ethyl acetate:hexane gave 2.5 g of product. MP 157° C.

Workup

  1. temperaturewas heated at 180°-190° C. for two hours
  2. temperatureto cool to a glass
  3. dissolutiondissolved
  4. washThe organic phase was washed with 0.5M sodium hydroxide solution and water
  5. dry with materialwas dried over anhydrous sodium sulphate
  6. customEvaporation of the solvent
  7. customunder reduced pressure and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5649160c095e4dae806a90a097b7ce6d
Source dataset
uspto-grants-1994_07
Patent number
US05326766

Reaction notes

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