4-Amino-m-cresol → 4-(4-Hydroxy-2-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 612198Notes

Reaction equation

HRID 612198 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].Cl.N1C=CC=CC=1.[NH2:25][C:26]1[C:27]([CH3:33])=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1>C(OCCO)C>[OH:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[C:27]([CH3:33])[CH:28]=1

Participants

5

Reactant 3

HCID 178194-Amino-m-cresolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224666394-(4-Hydroxy-2-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 90.9%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in Example 286, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile in 15 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 147.8 mg (1.2 mmol) of 4-amino-m-cresol to give 304.6 mg (90.9%) of the product as a salmon solid, m.p.>250° C., mass (electrospray, m/e): M+H 335.9

Sources & evidence

ORD record
ord-f9bc3fbd838c418bbff3305ac6cefdf5
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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