Thionyl Chloride → 3-(chloromethyl)-N-ethyl-6-methoxyquinolin-2-amine

HRID 1620206Notes

Reaction equation

HRID 1620206 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH2:14]O)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2].O=S(Cl)[Cl:20]>C(Cl)Cl>[ClH:20].[Cl:20][CH2:14][C:13]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:16][CH3:17])=[CH:8][CH:7]=2.[Cl:20][CH2:14][C:13]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:16][CH3:17])=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182241(2-(Ethylamino)-6-methoxyquinolin-3-yl)methanol2×

Product 2

HCID 681822213-(chloromethyl)-N-ethyl-6-methoxyquinolin-2-amineYield 100%HCID 681824593-(chloromethyl)-N-ethyl-6-methoxyquinolin-2-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-(ethylamino)-6-methoxyquinolin-3-yl)methanol SLA 28164 (1.150 g, 4.95 mmol) in dry CH2Cl2 (127 mL) a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (7.18 mL, 99.0 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. 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)-N-ethyl-6-methoxyquinolin-2-amine hydrochloride SLA 28166 as a yellow solid (1.43 g, 100% yield) that was used immediately in the next step.

Workup

  1. concentrationthen concentrated to dryness 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-5eaa438b43c142139566a93b197517a4
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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