Ethyl Acetate → 2-Methyl-4-((pyridin-2-ylmethyl)amino)quinolin-8-ol

HRID 889225Notes

Reaction equation

HRID 889225 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(OCC)(=O)C>CS(C)=O>[CH3:13][C:4]1[CH:3]=[C:2]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 195092-PyridinemethanamineHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 667608362-Methyl-4-((pyridin-2-ylmethyl)amino)quinolin-8-olYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of the 4-chloro-2-methylquinolin-8-ol (2.00 g, 10.3 mmol) and 2-aminomethyl pyridine (3.35 g, 30.9 mmol) in DMSO (5 mL) was heated at 160° C. for 2 h under nitrogen atmosphere. The mixture was cooled, poured into ice/NaHCO3 and extracted with ethyl acetate and dichloromethane. Evaporation gave a crude mixture that was mixed with ethyl acetate. The yellow solid precipitated and was filtered and dried to give 1.20 g of 2-methyl-4-((pyridin-2-ylmethyl)amino)quinolin-8-ol (44%). MS (+APCI) 266 (M+). 1H-NMR (CDCl3, δ): 8.56 (m, 1H), 7.79 (t, J=6.0 Hz, 1H), 7.75 (dt, J=2.0, 7.6 Hz, 1H), 7.63 (dd, J=1.2, 8.4 Hz, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.25 (m, 2H), 6.96 (d, J=7.6 Hz, 1H), 6.29 (s, 1H), 4.62 (d, J=6.0 Hz, 2H), 2.41 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate and dichloromethane
  3. customEvaporation
  4. customgave a crude mixture that
  5. customThe yellow solid precipitated
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-cdcaf560c9a74b7086ce5550ea038112
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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