4-Amino-2,5-dimethylphenol → HCID 19598399, compound

HRID 612194Notes

Reaction equation

HRID 612194 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=C[CH:20]=1.[NH2:25][C:26]1[C:31](C)=[CH:30][C:29]([OH:33])=[C:28]([CH3:34])[CH:27]=1>C(OCCO)C>[OH:33][C:29]1[C:28]([CH3:34])=[CH:27][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])=[CH:31][C:30]=1[CH3:20]

Participants

5

Reactant 3

HCID 765444-Amino-2,5-dimethylphenolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 19598399HCID 19598399, compoundYield 66.7%

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 164.6 mg (1.2 mmol) of 4-amino-2,5-dimethylphenol to give 232.9 mg (66.7%) of the product as a light brown solid, m.p. 234-236° C., mass (electrospray, m/e): M+H 349.9.

Sources & evidence

ORD record
ord-ccc4160a9fd14b4b8f7377fe63f0737f
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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