Thionyl Chloride → HCID 68182181, compound

HRID 1620261Notes

Reaction equation

HRID 1620261 reaction equation
[CH2:1]([C:3]1[C:12]([CH2:13]O)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:15][CH3:16])[CH:9]=2)[N:4]=1)[CH3:2].O=S(Cl)[Cl:19]>C(Cl)Cl>[ClH:19].[Cl:19][CH2:13][C:12]1[C:3]([CH2:1][CH3:2])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:15][CH3:16])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182277HCID 68182277, compound2×

Product 1

HCID 68182181HCID 68182181, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-ethyl-6-methoxyquinolin-3-yl)-methanol SMA 44008 (150 mg, 0.69 mmol) in dry CH2Cl2 (20 mL) at 0° C. under N2 in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.0 mL, 13.8 mmol) and the mixture was stirred 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-2-ethyl-6-methoxyquinoline hydrochloride SMA 44014 as a brown solid (197 mg, >100% yield).

Workup

  1. customThe volatiles were then removed at 40° C. under vacuum
  2. 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-a65c585c493f4965ae1036adce6c8ca6
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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