2,4-Dichloro-5-methoxyaniline → HCID 23498103, compound

HRID 1837340Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:17])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Cl:20][C:21]1[CH:27]=[C:26]([Cl:28])[C:25]([O:29][CH3:30])=[CH:24][C:22]=1[NH2:23].Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:20][C:21]1[CH:27]=[C:26]([Cl:28])[C:25]([O:29][CH3:30])=[CH:24][C:22]=1[NH:23][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:17])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19]

Participants

Conditions

Temperature: 102.5 °C

Procedure

A mixture of 4-chloro-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile (1.00 g, 3.59 mmol), 2,4-dichloro-5-methoxyaniline (727 mg, 3.77 mmol) and pyridine hydrochloride (620 mg, 5.34 mmol) in 18 mL of 2-ethoxyethanol is heated at 100-105° C. for 2 hours. The reaction mixture is cooled to room temperature and then poured into ice cold saturated sodium bicarbonate. The solids are collected, washed with water and then treated with methanol and dichloromethane. The mixture is filtered and the filtrate is concentrated. The solid residue is slurried with hexane, and the solids are collected by filtration to provide 1.15 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 170-172° C.

Workup

temperatureThe reaction mixture is cooled to room temperature
additionpoured into ice cold saturated sodium bicarbonate
customThe solids are collected
washwashed with water
additiontreated with methanol and dichloromethane
filtrationThe mixture is filtered
concentrationthe filtrate is concentrated
filtrationthe solids are collected by filtration

Sources & evidence

ORD record: ord-73be8553bc6c44638d6f35d9b0f2d434
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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