2,4-Dichloro-5-methoxyaniline → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-3-quinolinecarbonitrile

HRID 1837349Notes

Reaction equation

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

Participants

Reactant 3

HCID 14766362,4-Dichloro-5-methoxyaniline

HCID 10176127Pyridinium chloride

HCID 234980814-Chloro-7-fluoroquinoline-3-carbonitrile

Product 1

HCID 234980954-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-3-quinolinecarbonitrileYield 48.2%

Procedure

Following the procedure of Reference Example 8, a mixture of 4-chloro-7-fluoro-3-quinolinecarbonitrile (2.10 g, 10.2 mmol), 2,4-dichloro-5-methoxyaniline (2.15 g, 11.2 mmol) and pyridine hydrochloride (1.18 g, 10.2 mmol) provides 1.78 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-3-quinolinecarbonitrile, mp 199-201° C.

Sources & evidence

ORD record: ord-45f7b4f7dad54d0daaaa0281dc5f4f14
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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