Thionyl Chloride → 3-(Chloromethyl)-6-ethoxy-N-ethylquinolin-2-amine hydrochloride

HRID 1620211Notes

Reaction equation

HRID 1620211 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH2:15][CH3:16])[C:8]([CH2:17]O)=[CH:7]2)[CH3:2].O=S(Cl)[Cl:21]>C(Cl)Cl>[ClH:21].[Cl:21][CH2:17][C:8]1[C:9]([NH:14][CH2:15][CH3:16])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182224(6-Ethoxy-2-(ethylamino)quinolin-3-yl)methanol2×

Product 1

HCID 681822793-(Chloromethyl)-6-ethoxy-N-ethylquinolin-2-amine hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-ethoxy-2-(ethylamino)quinolin-3-yl)methanol SLA 41040 (0.457 g, 1.86 mmol) in dry CH2Cl2 (40 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (2.63 mL, 37.1 mmol). The mixture was stirred for 4 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-ethoxy-N-ethylquinolin-2-amine hydrochloride SLA 41042 as a yellow solid (552 mg, 99% 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-910e948a933040f58fb418bbd49978c7
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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