Thionyl Chloride → 3-(Chloromethyl)-6-methoxy-N-(2,2,2-trifluoroethyl)quinolin-2-amine hydrochloride

HRID 1620223Notes

Reaction equation

HRID 1620223 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][C:15]([F:18])([F:17])[F:16])[C:7]([CH2:19]O)=[CH:6]2.O=S(Cl)[Cl:23]>C(Cl)Cl>[ClH:23].[Cl:23][CH2:19][C:7]1[C:8]([NH:13][CH2:14][C:15]([F:18])([F:17])[F: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 68182332(6-Methoxy-2-(2,2,2-trifluoroethylamino)quinolin-3-yl)methanol2×

Product 1

HCID 681821763-(Chloromethyl)-6-methoxy-N-(2,2,2-trifluoroethyl)quinolin-2-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methoxy-2-(2,2,2-trifluoroethylamino)quinolin-3-yl)methanol SLA 41068 (1.45 g, 5.07 mmol) in dry CH2Cl2 (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (7.35 mL, 101.3 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-(2,2,2-trifluoroethyl)quinolin-2-amine hydrochloride SLA 41070 as a yellow solid (1.74 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-06340ac989ea468780759021578245dc
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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