2,4-Dichloro-5-methoxyaniline → HCID 10368288, compound

HRID 1837368Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][C:10]([C:21]#[N:22])=[C:9]2Cl)[CH2:2][CH2:3][CH3:4].[Cl:24][C:25]1[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:26]=1[NH2:27].Cl.N1C=CC=CC=1>C(OCCO)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][C:10]([C:21]#[N:22])=[C:9]2[NH:27][C:26]1[CH:28]=[C:29]([O:33][CH3:34])[C:30]([Cl:32])=[CH:31][C:25]=1[Cl:24])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-butoxy-4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile (184 mg, 0.55 mmol), 2,4-dichloro-5-methoxyaniline (127 mg, 0.66 mmol) and pyridine hydrochloride (76 mg, 0.66 mmol) in 5 mL of 2-ethoxyethanol is heated at 120° C. for 7 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo. Diethyl ether is added to the residue and the solids are collected and suspended in saturated aqueous sodium bicarbonate. After stirring for 1 hour the solids are collected by filtration and washed with water. Purification by preparatory thin layer chromatography, eluting with 7% methanol in dichloromethane provides 93 mg of 6-butoxy-4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 166-167° C.

Workup

temperatureThe reaction mixture is cooled to room temperature
concentrationconcentrated in vacuo
additionDiethyl ether is added to the residue
customthe solids are collected
filtrationare collected by filtration
washwashed with water
customPurification by preparatory thin layer chromatography
washeluting with 7% methanol in dichloromethane

Sources & evidence

ORD record: ord-f1530086bcee4f619b1b0213711b7d87
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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