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

HRID 1620198Notes

Reaction equation

HRID 1620198 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][CH3:14])[C:7]([CH2:15]O)=[CH:6]2.O=S(Cl)[Cl:19]>C(Cl)Cl>[ClH:19].[Cl:19][CH2:15][C:7]1[C:8]([NH:13][CH3:14])=[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 68182278(6-Methoxy-2-(methylamino)quinolin-3-yl)methanol2×

Product 1

HCID 681822493-(chloromethyl)-6-methoxy-N-methylquinolin-2-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methoxy-2-(methylamino)quinolin-3-yl)methanol SLA 28152 (0.906 g, 4.15 mmol) in dry CH2Cl2 (100 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (6.03 mL, 83.1 mmol). The mixture was stirred for 1 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-methylquinolin-2-amine hydrochloride SLA 28154 (1.20 g, >100%) 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-38e10434671241c9a8aa66c8e870f220
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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