Thionyl Chloride → HCID 68182032, compound

HRID 1620289Notes

Reaction equation

HRID 1620289 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12]O)[CH:8]=2)[N:3]=1.O=S(Cl)[Cl:16]>C(Cl)Cl>[ClH:16].[Cl:16][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2795481(2-methylquinolin-6-yl)methanol2×

Product 1

HCID 68182032HCID 68182032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-methylquinolin-6-yl)methanol SLA 47080A (0.973 g, 5.62 mmol) in dry CH2Cl2 (40 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.15 mL, 112 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 6-(chloromethyl)-2-methylquinoline hydrochloride SLA 47080B as a yellow solid (1.30 g, quant).

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-0120dee34662454b9db419dc6e2a0035
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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