Potassium Hydroxide → 4-Chloro-6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinoline

HRID 880039Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[NH:9][CH:8]=[CH:7][C:6]2=O.O=P(Cl)(Cl)[Cl:25].[OH-].[K+]>C(#N)C>[Cl:25][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Intermediate VI (63 g, 0.198 mol) and POCl3 (5 v/w, 315 in L) were added to acetonitrile (5 v/w, 315 mL). The mixture was warmed up to 85° C. to react under reflux for 6 h. After completion of the reaction, the reaction solution was cooled. POCl3 and acetonitrile were evaporated off to produce a grey viscous solid. This solid was added to a great deal of ice-water mixture, adjusted with a 10% KOH solution to a pH of 10, and extracted with CH2Cl2 (200 mL×3). The organic layer was collected, dried over anhydrous sodium sulfate, and cooled after evaporating off the solvate to produce an off-white solid (58 g) in a yield of 87.3%.

Workup

customto react
temperatureunder reflux for 6 h
customAfter completion of the reaction
temperaturethe reaction solution was cooled
customPOCl3 and acetonitrile were evaporated off
customto produce a grey viscous solid
extractionextracted with CH2Cl2 (200 mL×3)
customThe organic layer was collected
dry with materialdried over anhydrous sodium sulfate
temperaturecooled
customafter evaporating off the solvate

Sources & evidence

ORD record: ord-4530c88dd840477099da7cb2e35a8f18
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993566B2

Reaction notes

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