Dimethylformamide → HCID 70097379, compound

HRID 868974Notes

Reaction equation

HRID 868974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:13]O)[CH:9]=[CH:8]2.CN(C)C=O.S(Cl)([Cl:22])=O>>[Cl:22][CH2:13][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[N:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 68578632(8-Methoxyquinolin-2-yl)methanol

Product 1

HCID 70097379HCID 70097379, compound

Procedure

A mixture of (8-methoxyquinolin-2-yl)methanol (1.0 g, 5.3 mmol) and N,N-dimethylformamide (39 mg, 0.53 mmol) in sulfurous dichloride (20 mL) was stirred at room temperature for 2 h. The reaction mixture was concentrated and ice water was added. The pH of the aqueous layer was adjusted to 7 with 10 N sodium hydroxide solution. The mixture was extracted with DCM (30 mL×3). The combined organic phase was dried with anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 0.66 g of the product as a yellow solid. MS (ESI): m/z 208.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionice water was added
  3. extractionThe mixture was extracted with DCM (30 mL×3)
  4. dry with materialThe combined organic phase was dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-1064e1d0d91d4137aa1ab9f266babd75
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

Loading…