Phosphorus oxychloride → 2-Chloroquinolin-6-ol
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=2)[N:1]=1Participants
3
Procedure
As set forth in reaction Scheme C, quinoline2,6-diol is chlorinated with POCl3 to obtain 2-chloroquinolin-6-ol, which is reacted with a desired amine substituent, in this case 4-bromo-3-methylaniline, and to obtain the amine substituted quinolinol. A mixture of the alcohol and potassium bis(trimethylsilyl)amide in dimethylformamide is reacted with a desired substituent at the alcohol group, in this case dimethylformamide, to obtain the desire product, in this case (4-{2-[(4-bromo-3-methylphenyl)amino](6-quinolyloxy)}(2-pyridyl))-N-methylcarboxamide.
Sources & evidence
- ORD record
- ord-6c0a61c1403b4f7abdb94bee08fd1f8d
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691866B2
Reaction notes
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