Potassium Carbonate → HCID 580807, compound

HRID 1863104Notes

Reaction equation

HRID 1863104 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:23][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[N:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133974-Chlorobenzyl alcoholHCID 2715792-Chloro-6-methoxy-8-nitroquinoline

Product 1

HCID 580807HCID 580807, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 48 g (0.2 mole) of 2-chloro-6-methoxy-8-nitroquinoline, 42.78 g (0.3 mole) of 4-chlorobenzyl alcohol, 27.6 g (0.2 mole) of anhydrous potassium carbonate, and 200 ml N,N-dimethyl formamide was heated under nitrogen at ca. 155°-160° for 18 hr. The mixture was cooled, diluted with ice water, stirred, collected, and washed with water. The crude solid was leached with a little 95% ethanol at 70° and then recrystallized from that solvent. A 84% yield of 2-(4-chlorobenzyloxy)-6-methoxy-8-nitroquinoline resulted; mp 129.5°-133.5°.

Workup

  1. temperaturewas heated under nitrogen at ca. 155°-160° for 18 hr
  2. temperatureThe mixture was cooled
  3. customcollected
  4. washwashed with water
  5. customwas leached with a little 95% ethanol at 70°
  6. customrecrystallized from that solvent

Sources & evidence

ORD record
ord-488f92dae41e4fdb83d8cfc62b0a67c6
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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