2-Amino-5-methylphenol → 4-(2-Hydroxy-4-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 612193Notes

Reaction equation

HRID 612193 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[CH:27]=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=1[OH:32]>C(OCCO)C>[OH:32][C:31]1[CH:30]=[C:29]([CH3:33])[CH:28]=[CH:27][C:26]=1[NH:25][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]

Participants

5

Reactant 3

HCID 760822-Amino-5-methylphenolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224666764-(2-Hydroxy-4-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 85.8%

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 10 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 6-amino-m-cresol to give 287.5 mg (85.8%) of the product as a light brown solid, m.p.>250° C., mass (electrospray, m/e): M+H 335.9.

Sources & evidence

ORD record
ord-790a273606d34abc96ea4658769f0d3d
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…