5-Amino-2-methoxyphenol → HCID 22466565, compound

HRID 1935100Notes

Reaction equation

HRID 1935100 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].Cl.N1C=CC=CC=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][CH3:32])=[C:28]([OH:30])[CH:29]=1>C(OCCO)C>[OH:30][C:28]1[CH:29]=[C:24]([NH:23][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])[CH:25]=[CH:26][C:27]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 743145-Amino-2-methoxyphenolHCID 10176127Pyridinium chlorideHCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 22466565HCID 22466565, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 274. A reaction mixture of 200.0 mg (0.92 mmol) of 4-chloro-8-methoxy-3-quinolinecarbonitrile, 105.7 mg (0.92 mmol) of pyridine hydrochloride and 140.6 mg (1.0 mmol) of 5-amino-2-methoxy-phenol in 10 mL of 2-ethoxyethanol was heated at 100° C. for 2 hr. The work up gave 261.6 mg (89.0%) of the product as a deep yellow solid, m.p. 138-140° C. (dec.), mass spectrum (electrospray, m/e): M+H 321.9.

Sources & evidence

ORD record
ord-db89b702bddc42bcb1eda2bc9209bbc4
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

Loading…