Pyridinium chloride → HCID 86694552, compound

HRID 714578Notes

Reaction equation

HRID 714578 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH:16]3[CH2:20][CH2:19][O:18][CH2:17]3)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]#[N:22].[Cl:23][C:24]1[CH:25]=[C:26]([NH2:38])[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1.Cl.N1C=CC=CC=1>C(O)(C)C>[Cl:23][C:24]1[CH:25]=[C:26]([NH:38][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH:16]4[CH2:20][CH2:19][O:18][CH2:17]4)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:21]#[N:22])[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1

Participants

5

Reactant 3

HCID 10176127Pyridinium chlorideHCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 86694549HCID 86694549, compound

Product 1

HCID 86694552HCID 86694552, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

To a single-neck reaction flask (500 ml) were added 4-chloro-6-nitro-7-(tetrahydrofuran-3-yl-oxy)quinoline-3-carbonitrile (5 g, 15.649 mmol), 3-chloro-4-(pyridin-2-yl-methoxy)benzenamine (4.037 g, 17.214 mmol) and pyridine hydrochloride (421 mg). To the flask was added isopropanol (150 ml). The mixture was stirred and refluxed for 2 hr at the temperature of 85° C. The reaction was stopped and cooled to the room temperature. The resultant mixture was filtered in vacuo. The filter cake was washed with mother liquor and dried in vacuo to give a yellow solid (5.988 g). Yield: 73.9%.

Workup

  1. temperaturecooled to the room temperature
  2. filtrationThe resultant mixture was filtered in vacuo
  3. washThe filter cake was washed with mother liquor
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9548072817794b5e89063add8933be28
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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