Methanol → 3-(chloromethyl)-N,N,6-trimethylquinolin-2-amine hydrochloride

HRID 1620194Notes

Reaction equation

HRID 1620194 reaction equation
CO.[CH3:3][N:4]([CH3:18])[C:5]1[C:14]([CH2:15]O)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:17])[CH:11]=2)[N:6]=1.O=S(Cl)[Cl:21]>C(Cl)Cl>[ClH:21].[Cl:21][CH2:15][C:14]1[C:5]([N:4]([CH3:18])[CH3:3])=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH3:17])=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 68182253(2-(Dimethylamino)-6-methylquinolin-3-yl)methanol

Product 1

HCID 681823133-(chloromethyl)-N,N,6-trimethylquinolin-2-amine hydrochlorideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(dimethylamino)-6-methylquinolin-3-yl)methanol RBO 40152 (900 mg, 4.16 mmol) in dry CH2Cl2 (30 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (3 mL, 42 mmol). The mixture was stirred for 3 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was coevaporated twice with CH2Cl2 (20 mL) at 40° C. under vacuum to give of 3-(chloromethyl)-N,N,6-trimethylquinolin-2-amine hydrochloride RBO 35154 as a yellow solid (558 mg, 50% yield).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. customwas coevaporated twice with CH2Cl2 (20 mL) at 40° C. under vacuum

Sources & evidence

ORD record
ord-22e0cdd5d5fd4a68b6fb5ddac08e7420
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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