Thionyl Chloride → HCID 68182410, compound

HRID 1620179Notes

Reaction equation

HRID 1620179 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH2:14]O)[CH:8]=[N:9]2)[CH3:2].O=S(Cl)[Cl:18]>C(Cl)Cl>[ClH:18].[Cl:18][CH2:14][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182175HCID 68182175, compound2×

Product 1

HCID 68182410HCID 68182410, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5-ethoxyquinolin-3-yl)methanol MDE 32076 (40 mg, 197 μmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (0.30 mL, 4.13 mmol) and the mixture was stirred for 30 min at 0° C. then for 2 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-5-ethoxyquinoline hydrochloride CCH 29192 as a yellow solid (51 mg, 100% yield).

Workup

  1. waitfor 2 h at RT
  2. customThe volatiles were then removed at 40° C. under vacuum
  3. concentrationthe residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-6671229c00264333b0420bbdf5f8805f
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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