Hydrochloric Acid → 3-Quinolinecarbonitrile, 4-hydroxy-
Reaction equation
CN([CH:4]=[N:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O)C.C[O-].[Na+].[C:19](#[N:21])[CH3:20].Cl>O.C1(C)C=CC=CC=1>[O:10]=[C:8]1[C:7]2[C:6](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:5][CH:4]=[C:20]1[C:19]#[N:21]Participants
7
Procedure
A stirred mixture of 1.03 g of methyl 2-(dimethylaminomethyleneamino)benzoate, 0.54 g of sodium methoxide, 1.04 ml of acetonitrile, and 10 ml of toluene was refluxed for 18 h. The mixture was cooled, treated with water, and brought to pH 3 by addition of dilute HCl. The resulting solid was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was recrystallized from ethanol to give a solid, mp 290-300° C.
Workup
- temperaturewas refluxed for 18 h
- temperatureThe mixture was cooled
- extractionThe resulting solid was extracted with ethyl acetate
- washThe extract was washed with water
- customdried
- customevaporated
- customThe residue was recrystallized from ethanol
- customto give a solid, mp 290-300° C.
Sources & evidence
- ORD record
- ord-27e5f83834ba43c1bf159db5906dea3a
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06002008
Reaction notes
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