Hydrochloric Acid → 1-(2,5-Dichloroquinolin-3-yl)ethanol

HRID 216801Notes

Reaction equation

HRID 216801 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:14])[N:3]=1.[CH3:15][Mg]Br.Cl>C1COCC1>[Cl:1][C:2]1[C:11]([CH:12]([OH:13])[CH3:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:14])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 157075292,5-Dichloroquinoline-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 577079561-(2,5-Dichloroquinolin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 2,5-dichloroquinoline-3-carbaldehyde (2.46 g, 11 mmol) in THF (70 mL) and submerged in an ice-bath. Added methylmagnesium bromide (5.4 mL, 16 mmol) and removed the ice-bath. After 10 min. the reaction mixture was poured into 1.0 N HCl and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was chromatographed on 80 g silica gel column with 0-40% EtOAc:Hex. The desired fractions were combined and concentrated to yield an off white, crystalline solid. 1H NMR (400 MHz, DCM-d2) δ ppm 1.60 (d, J=6.26 Hz, 3H) 2.35 (br. s., 1H) 5.36 (q, J=6.39 Hz, 1H) 7.61-7.67 (m, 2H) 7.87-7.94 (m, 1H) 8.75 (s, 1H). LC-MS (+esi, M+H+=242.1).

Workup

  1. customsubmerged in an ice-bath
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on 80 g silica gel column with 0-40% EtOAc
  7. concentrationconcentrated
  8. customto yield an off white, crystalline solid

Sources & evidence

ORD record
ord-d43757cfd6bd409f816602001bed92ad
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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