Thionyl Chloride → HCID 18919704, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[N:15]=[CH:14][C:13]([CH3:19])=[CH:12][C:11]=3[CH:10]2O)=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>>[Cl:23][CH:10]1[CH:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:18][CH2:17][C:16]2[N:15]=[CH:14][C:13]([CH3:19])=[CH:12][C:11]1=2Participants
Procedure
5,6,7,8-Tetrahydro-6-((4-fluorophenyl)methyl-5-hydroxy-3-methylquinoline (2.4 g prepared according to Example 13) was dissolved in thionyl chloride (15 ml) and left to stir for 3 hours. The solvent was evaporated the residue diluted with water. The aqueous solution was basified with solid K2CO3 and extracted into ethyl acetate. The organic solution was dried (Na2SO4) and evaporated to give 5,6,7,8-tetrahydro-5-chloro-6-(4-fluorophenyl)methyl-3-methylquinoline (2.13 g). This was dissolved in THF (20 ml) and L-Selectride (1M solution in THF, 20 ml) was added. The reaction mixture was left to stir for 20 hours and acetic acid (5 ml) was added. The solvent was evaporated under reduced pressure and the residue dissolved in 2N HCI. The acidic solution was washed with ethyl acetate and basified with solid K2CO3. The basic solution was extracted into ethyl acetate, dried (MgSO4), evaporated and the residue dissolved in methanol and ethereal hydrogen chloride added. The solvent was evaporated under reduced pressure and the methanol was replaced and evaporated three times. The residue was recrystallised from EPA/ethyl acetate to give the title compound as the monohydrochloride salt (1.12 g), mp=168°-169° C.
Workup
- waitleft
- customThe solvent was evaporated the residue
- additiondiluted with water
- extractionextracted into ethyl acetate
- dry with materialThe organic solution was dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-de38a655a193488ca135ff5f50907b40
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753676
Reaction notes
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