4-Aminoresorcinol → 4-(2,4-Dihydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 612205

Reaction equation

HRID 612205 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:32]=[CH:31][C:29]([OH:30])=[CH:28][C:27]=1[OH:33]>C(OCCO)C>[OH:33][C:27]1[CH:28]=[C:29]([OH:30])[CH:31]=[CH:32][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 4328274-AminoresorcinolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224665474-(2,4-Dihydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 98%

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 12 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 210.0 mg (1.3 mmol) of 4-aminoresorcinol to give 330.4 mg (98.0%) of the product as a deep purple solid, m.p.>250° C., mass (electrospray, m/e): M+H 337.9.

Sources & evidence

ORD record
ord-8ca0a800677148f0a4b96e35050ed9a0
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Linked notes

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