2,4-Dichloro-5-methoxyaniline → HCID 178486403, compound

HRID 2213827Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:23]=1[NH2:24].Cl.N1C=CC=CC=1>C(OCCO)C.C(=O)(O)[O-].[Na+]>[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH3:31])=[CH:25][C:23]=1[NH:24][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 0.7 g (2.46 mmol) of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, 0.57 g (2.95 mmol) of 2,4-dichloro-5-methoxyaniline and 0.28 g (2.46 mmol) of pyridine hydrochloride in 7 mL of 2-ethoxyethanol is heated at 120° C. for 2 hours, then cooled to room temperature. The product mixture is diluted with saturated solution of sodium bicarbonate and stirred for 15 minutes. The resulting solid is collected by filtration, washed with water and dried. The crude product is purified by silica gel chromatography, utilizing a 98:2 to 90:10 gradient of methylene chloride/methanol to give 0.71 g of 4-(2,4-dichloro-5-methoxyphenylamino)-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp, 238–240° C.

Workup

temperaturecooled to room temperature
filtrationThe resulting solid is collected by filtration
washwashed with water
customdried
customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record: ord-5e1cc48af3284ba49d124e503bd5f601
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105531B2

Reaction notes

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