Thionyl Chloride → HCID 57556155, compound

HRID 2074492Notes

Reaction equation

HRID 2074492 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH:22]=O)=[CH:7]2.CC1C=CC=C2C=1N=C(C1C=CC=CC=1C(F)(F)F)C(CO)=C2.O=S(Cl)[Cl:49]>C1COCC1.C(Cl)(Cl)Cl>[Cl:49][CH2:22][C:8]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:20])([F:21])[F:19])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 575561608-Methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehydeHCID 57556178(8-Methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol

Product 1

HCID 57556155HCID 57556155, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure B using 8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (1.6541 g, 5.25 mmol) and solid NaBH (0.2977 g, 7.87 mmol, 1.5 eq) in THF (26 mL) followed by Procedure C using the crude (8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol and SOCl2 (1.9 mL, 26.23 mmol, 5 eq) in CHCl3 (26 mL). After purification, 3-(chloromethyl)-8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline was obtained as yellow syrup. 1H NMR (DMSO-d6) δ ppm 8.60 (1 H, s), 7.92 (2 H, dd, J=11.5, 8.0 Hz), 7.72-7.85 (2 H, m), 7.67 (2 H, dd, J=14.3, 7.2 Hz), 7.54-7.62 (1 H, m), 4.71 (2 H, dd, J=89.8, 11.9 Hz), 2.62 (3 H, s). Mass Spectrum (ESI) m/e=336.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-a6731650070344128287c008c3bc9e44
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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