Thionyl Chloride → 3-(Chloromethyl)-6-methoxy-N-propylquinolin-2-amine hydrochloride

HRID 1620202Notes

Reaction equation

HRID 1620202 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][CH3:16])[C:7]([CH2:17]O)=[CH:6]2.O=S(Cl)[Cl:21]>C(Cl)Cl>[ClH:21].[Cl:21][CH2:17][C:7]1[C:8]([NH:13][CH2:14][CH2:15][CH3:16])=[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 68182269(6-Methoxy-2-(propylamino)quinolin-3-yl)methanol2×

Product 1

HCID 681822053-(Chloromethyl)-6-methoxy-N-propylquinolin-2-amine hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methoxy-2-(propylamino)quinolin-3-yl)methanol SLA 28174 (1.45 g, 5.88 mmol) in dry CH2Cl2 (115 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.53 mL, 118 mmol). The mixture was stirred for 2 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-propylquinolin-2-amine hydrochloride SLA 28178 (1.28 g, 82% yield) as a yellow solid.

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-828ee02782934d78932d7b7b157a8338
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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