5-Amino-2-chloro-4-fluorophenol → 4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-7-(2-chloro-ethoxy)-6-methoxy-quinoline-3-carbonitrile

HRID 1934953Notes

Reaction equation

HRID 1934953 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].C(=O)([O-])OC.[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH2:30])=[C:28]([F:34])[CH:27]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:25][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH:30][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][Cl:1])=[C:6]([O:18][CH3:19])[CH:7]=3)[N:12]=[CH:11][C:10]=2[C:15]#[N:16])=[C:28]([F:34])[CH:27]=1

Participants

6

Reactant 4

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 4585885MethylcarbonateHCID 10176127Pyridinium chlorideHCID 111092524-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 224667484-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-7-(2-chloro-ethoxy)-6-methoxy-quinoline-3-carbonitrile

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, 2.46 g of the methyl carbonate of 4-chloro-2-fluoro-5-hydroxy-aniline, and 1.18 g of pyridine hydrochloride in 31 ml of 2-ethoxyethanol, 2.2 g of the title compound was obtained as a tan solid: mass spectrum (electrospray, m/e) M+H 421.9.

Sources & evidence

ORD record
ord-2654b2f85f3e44a4a25087e547fa138d
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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