Thionyl Chloride → 4-(Chloromethyl)quinoline--hydrogen chloride (1/1)

HRID 1620171Notes

Reaction equation

HRID 1620171 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11]O)=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)C=C(CO)C=1.O=S(Cl)[Cl:27]>C(Cl)Cl>[ClH:27].[Cl:27][CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 804794-(Hydroxymethyl)quinolineHCID 12662983(Quinolin-3-yl)methanol

Product 1

HCID 230016194-(Chloromethyl)quinoline--hydrogen chloride (1/1)Yield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of quinolin-4-ylmethanol MDE 32014 (0.28 g, 1.76 mmol) in dry CH2Cl2 (18 mL) at 0° C. under N2 in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (2.6 mL, 36.0 mmol) and the mixture was stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 4-(chloromethyl)quinoline hydrochloride MDE 32016 as an off-white solid (246 mg, 65% yield).

Workup

  1. customThe volatiles were then removed 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-4bc7e43cc3ba45d4a937210ae4f7bfa0
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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