Thionyl Chloride → 3-(Chloromethyl)-N-isopropyl-6-methoxyquinolin-2-amine hydrochloride

HRID 1620216Notes

Reaction equation

HRID 1620216 reaction equation
[CH:1]([NH:4][C:5]1[C:14]([CH2:15]O)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2].O=S(Cl)[Cl:21]>C(Cl)Cl>[ClH:21].[Cl:21][CH2:15][C:14]1[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:17][CH3:18])=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182178(2-(Isopropylamino)-6-methoxyquinolin-3-yl)methanol2×

Product 1

HCID 681822153-(Chloromethyl)-N-isopropyl-6-methoxyquinolin-2-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-(isopropylamino)-6-methoxyquinolin-3-yl)methanol SLA 28188 (1.41 g, 5.72 mmol) in dry CH2Cl2 (115 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.30 mL, 114 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)-N-isopropyl-6-methoxyquinolin-2-amine hydrochloride SLA 28190 as a yellow solid (1.79 g, >100% yield).

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-0a0595ec8c684c198a3caf43a0a0bdd6
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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