Water → HCID 15917388, compound

HRID 1758138Notes

Reaction equation

HRID 1758138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](O)[C:5](=[CH:7][CH:8]=1)[OH:6].Cl[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].O>CN(C)C=O.ClCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)=[C:7]([O:21][C:18]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 99584-MethylcatecholHCID 11430Potassium CarbonateHCID 276852,5-Dichloropyridine

Product 1

HCID 15917388HCID 15917388, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8005Butyl ChlorideSolvent

Procedure

In 40 ml of dimethylformamide, a mixture of 4.0 grams (0.032 mole) 4-methylcatechol, 12.0 grams 2,5-dichloropyridine, and 12.0 grams of potassium carbonate was heated between 140° and 145° overnight. To the reaction mixture at room temperature was added excess H2O and the resulting aqueous mixture was extracted with ethyl ether (200 ml) which was washed with H2O (2X), saturated NaHCO3, brine, dried (MgSO4), filtered, and the solvent evaporated to yield an oil. Chromatography on a silica gel column using 1-chlorobutane as the eluent gave 5.0 grams of a white solid, m.p. 87°-90°; ir (Nujol): 6.30 (C=N), 9.10, 12.25 microns; NMR (CDCl3): δ2.35 (s, 3H, CH3), 6.60 (d, 2H, pyridine ring protons), 7.00 (broads, 3H, ArH), 7.45 (AB quartet, 2H, pyridine ring protons), 7.95 (d, 2H, pyridine ring protons).

Workup

  1. temperaturewas heated between 140° and 145° overnight
  2. extractionthe resulting aqueous mixture was extracted with ethyl ether (200 ml) which
  3. washwas washed with H2O (2X), saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto yield an oil

Sources & evidence

ORD record
ord-93a9de83292343c2ba5fa2938b76ba11
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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