Ammonium Chloride → HCID 19381193, compound

HRID 2209507Notes

Reaction equation

HRID 2209507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:18]=[O:19])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.[CH3:20][Li].[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:18]([OH:19])[CH3:20])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 19381162HCID 19381162, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19381193HCID 19381193, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

8-(3-Chlorophenyl)-6-quinolincarbaldehyde (0.8 g) was dissolved in 20 mL of tetrahydrofuran and cooled to -78° C. Methyllithium (4.5 mL, 1.4M) in diethyl ether was added dropwise to the solution over 5 minutes, stirred for 20 minutes, poured into 50 mL of saturated ammonium chloride, and stirred for 5 minutes. The solution was extracted with ethyl acetate (2×75 mL). The extracts were combined and dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (30:70 ethyl acetate:hexanes) to obtain 0.72 g of 8-(3-chlorophenyl)-6-(1-hydroxyethyl)quinoline as a yellow oil.

Workup

  1. stirringstirred for 5 minutes
  2. extractionThe solution was extracted with ethyl acetate (2×75 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-10f5bb2e22a849408db84e8e74e6d3a9
Source dataset
uspto-grants-1995_10
Patent number
US05455252

Reaction notes

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