Methylamine → 2-(Methylamino)quinolin-8-ol

HRID 493333Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][CH3:14]>CCO>[CH3:14][NH:13][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-8-hydroxyquinoline* (2.0 g, 11. I mmol) in EtOH (40 mL) was added H2NMe (40% aqueous solution, 40 mL, 464 mmol). The mixture was heated in a sealed Pyrex tube at 100° C. for 24 h. The solvent was evaporated and the resulting crude product was purified by column chromatography [gradient: CH2Cl2/MeOH (99:1) to 1% NH4OH in CH2Cl2/MeOH (80 20)] to give the title compound as a black-green solid Yield 1 31 g (67%), MS m/z 174 (M)+. Anal. (C10H10N2O) C, H, N

Workup

customThe solvent was evaporated
customthe resulting crude product was purified by column chromatography [gradient: CH2Cl2/MeOH (99:1) to 1% NH4OH in CH2Cl2/MeOH (80 20)]

Sources & evidence

ORD record: ord-e3d7154dc74b42578604ae75c4777b5a
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534794B2

Reaction notes

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