Thionyl Chloride → HCID 68182194, compound

HRID 1620183Notes

Reaction equation

HRID 1620183 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([CH2:14]O)[CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH3:2].O=S(Cl)[Cl:18]>C(Cl)Cl>[ClH:18].[Cl:18][CH2:14][C:9]1[CH:10]=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182302HCID 68182302, compound2×

Product 1

HCID 68182194HCID 68182194, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (7-ethoxyquinolin-3-yl)methanol MDE 32072 (88 mg, 433 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 (0.64 mL, 8.82 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)-7-ethoxyquinoline hydrochloride CCH 29190 as a brown solid (113 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-a12013da96204960be24a3900f31a4fc
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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