5-Amino-2-methylphenol → HCID 22466651, compound

HRID 612184Notes

Reaction equation

HRID 612184 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.[OH:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[CH3:31])[NH2:27]>C(OCCO)C>[OH:23][C:24]1[CH:25]=[C:26]([NH:27][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:28]=[CH:29][C:30]=1[CH3:31]

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 10176127Pyridinium chlorideHCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 22466651HCID 22466651, compoundYield 89.4%

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 328.0 mg (1.5 mmol) of 4-chloro-8-methoxy -3-quinolinecarbonitrile, 173.3 mg (1.5 mmol) of pyridine hydrochloride and 203.2 mg (1.7 mmol) of 3-hydroxy-4-methylaniline in 15 mL of 2-ethoxyethanol was heated at 100° C. for 1.5 hr. After the work up, 407.7 mg (89.4%) of the product was obtained as a yellow solid, m.p. 148-150° C., mass spectrum (electrospray, m/e): M+H 306.9.

Sources & evidence

ORD record
ord-3c51fe34f00541989f43670bffe29721
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…