Thionyl Chloride → 3-(chloromethyl)-6-methoxy-N-(2-methoxyethyl)quinolin-2-amine hydrochloride

HRID 1620282Notes

Reaction equation

HRID 1620282 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][CH2:14][CH2:15][O:16][CH3:17])[C:7]([CH2:18]O)=[CH:6]2.O=S(Cl)[Cl:22]>C(Cl)Cl>[ClH:22].[Cl:22][CH2:18][C:7]1[C:8]([NH:13][CH2:14][CH2:15][O:16][CH3:17])=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182190(6-Methoxy-2-(2-methoxyethylamino)quinolin-3-yl)methanol2×

Product 1

HCID 681822733-(chloromethyl)-6-methoxy-N-(2-methoxyethyl)quinolin-2-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methoxy-2-(2-methoxyethylamino)quinolin-3-yl)methanol SLA 47064A (0.90 g, 3.43 mmol) in dry CH2Cl2 (30 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (4.98 mL, 68.6 mmol). The mixture was stirred for 1.5 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-6-methoxy-N-(2-methoxyethyl)quinolin-2-amine hydrochloride SLA 47064 as a yellow solid (1.13 g, 100%).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. concentrationThe residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-b9dddc3c117c484bb7a5979aa813ece1
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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