4-Aminophenethyl alcohol → HCID 22466741, compound

HRID 1935116Notes

Reaction equation

HRID 1935116 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:34]=[CH:33][C:29]([CH2:30][CH2:31][OH:32])=[CH:28][CH:27]=1>C(OCCO)C>[OH:32][CH2:31][CH2:30][C:29]1[CH:33]=[CH:34][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:27][CH:28]=1

Participants

5

Reactant 3

HCID 669044-Aminophenethyl alcoholHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466741HCID 22466741, compoundYield 93.9%

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 12 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 178.3 mg (1.3 mmol) of 4-aminophenethyl alcohol to give 327.8 mg (93.9%) of the product as an off white yellow solid, m.p. 208-210° C., mass (electrospray, m/e): M+H 349.9.

Sources & evidence

ORD record
ord-d7abb898427f48b1881cca997356627a
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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