Thionyl Chloride → HCID 68993386, compound

HRID 2196592Notes

Reaction equation

HRID 2196592 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15]O.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[ClH:19].[Cl:19][CH2:15][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59756873HCID 59756873, compound

Product 1

HCID 68993386HCID 68993386, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

(6,7-Dimethoxyquinolin-4-yl)methanol (1.11 g, 5.07 mmol) was dissolved in thionyl chloride (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes then warmed to room temperature and stirred for 3.5 hours. The reaction mixture was diluted with benzene (20 ml) then concentrated under vacuum. The remaining solid was triturated with benzene then dried under high vacuum to afford 1.35 g of 4-(chloromethyl)-6,7-dimethoxyquinoline hydrochloride as a yellow solid. MS (ESI, pos. ion) m/z: 238.0 (M+1).

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred for 3.5 hours
  3. concentrationthen concentrated under vacuum
  4. customThe remaining solid was triturated with benzene
  5. customthen dried under high vacuum

Sources & evidence

ORD record
ord-2b1162627fa64f17aa9bf5a47e77dcea
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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