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

HRID 989382

Reaction equation

HRID 989382 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

6

Reactant 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 178486400HCID 178486400, compound

Product 1

HCID 178486403HCID 178486403, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 516892Sodium BicarbonateSolvent

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

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-e2d580160bfb4dcea4b7e35feca411e0
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Linked notes

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