Hydrochloric Acid → 3-Fluoro-4-[6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinolin-4-oxy]aniline

HRID 68536Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[O:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1>[Fe].CCO>[F:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1)[NH2:9]

Participants

Conditions

Temperature: 80 °C

Procedure

Iron powder (61.42 g, 1.1 mol) and hydrochloric acid (6 mL) were added to 90% EtOH (25v/w, 1210 mL). The mixture was warmed up to 80° C. and stirred for 15 min. Then Intermediate VIII (48.42 g, 0.11 mol) was added in batch to the reaction solution. After the addition completion, the reaction was conducted under reflux for 2 h. After completion of the reaction, the reaction was filtered by suction when it is still hot. The filtrate was collected. The solvate was evaporated off to produce a yellow solid (43 g) in a yield of 95%.

Workup

temperatureunder reflux for 2 h
customAfter completion of the reaction
filtrationthe reaction was filtered by suction when it
customThe filtrate was collected
customThe solvate was evaporated off

Sources & evidence

ORD record: ord-790b59523fa345bbac27cb895099891d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822465B2

Reaction notes

Loading…