5-Amino-2-methylphenol → 7-(2-Chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1934952Notes

Reaction equation

HRID 1934952 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](Cl)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19].[OH:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[CH3:28])[NH2:24].Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:24][C:23]3[CH:25]=[CH:26][C:27]([CH3:28])=[C:21]([OH:20])[CH:22]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 10176127Pyridinium chlorideHCID 111092524-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 224666497-(2-Chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrileYield 67.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

By using the above method, starting with 3 g of 7-(2-chloro-ethoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile, 1.37 g of 3-hydroxy-4-methyl-aniline, and 1.2 g of pyridine hydrochloride in 31 ml of 2-ethoxyethanol, 2.6 g of the title compound was obtained as a crystalline solid: mass spectrum (electrospray, m/e) M+H 383.9.

Sources & evidence

ORD record
ord-efef8308e53441d3bbecc37be1acc8d1
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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