2-Amino-4-methylphenol → HCID 22466625, compound

HRID 1935113Notes

Reaction equation

HRID 1935113 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:31]([OH:32])=[CH:30][CH:29]=[C:28]([CH3:33])[CH:27]=1>C(OCCO)C>[OH:32][C:31]1[CH:30]=[CH:29][C:28]([CH3:33])=[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 72642-Amino-4-methylphenolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466625HCID 22466625, compoundYield 94%

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 2-amino-p-cresol to give 315.0 mg (94.0%) of the product as a yellow solid, m.p. 198-200° C., mass (electrospray, m/e): M+H 335.8.

Sources & evidence

ORD record
ord-37187966b13d4c6e8196087f3af554a7
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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