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

HRID 1620234Notes

Reaction equation

HRID 1620234 reaction equation
COC1C=C2C(=CC=1)N=C(NCCC)C(CO)=C2.[CH:19]([NH:22][C:23]1[C:32]([CH2:33]O)=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:35][CH3:36])[CH:29]=2)[N:24]=1)([CH3:21])[CH3:20].O=S(Cl)[Cl:39]>C(Cl)Cl>[ClH:39].[Cl:39][CH2:33][C:32]1[C:23]([NH:22][CH:19]([CH3:21])[CH3:20])=[N:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([O:35][CH3:36])=[CH:27][CH:26]=2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 68182178(2-(Isopropylamino)-6-methoxyquinolin-3-yl)methanolHCID 68182269(6-Methoxy-2-(propylamino)quinolin-3-yl)methanol

Product 1

HCID 681822153-(Chloromethyl)-N-isopropyl-6-methoxyquinolin-2-amine hydrochlorideYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-methoxy-2-(propylamino)quinolin-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 of 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-a67339baee3245838e3ddf6bcfa563f2
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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