Dimethylformamide → HCID 12849341, compound

HRID 1723481Notes

Reaction equation

HRID 1723481 reaction equation
[H-].[Na+].CN(C)C=O.[Cl:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[CH:13][C:14]=1[Cl:15].Cl[C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]>O>[Cl:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:16][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72583,4-DichlorophenolHCID 24758Sodium hydrideHCID 762582-Chloronicotinic acid

Product 1

HCID 12849341HCID 12849341, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride dispersion, 60% by weight (2.54 grams, 63.47 mmol) is placed into a 125 ml round bottom flask equipped with a stir bar and condenser under nitrogen and is charged with 32 ml of dimethyl formamide. 3,4-Dichlorophenol (5.17 grams, 31.73 mmol) is added portionwise over five minutes. During this addition, an exotherm and vigorous gas evolution are observed. The reaction is allowed to stir for five minutes. 2-Chloronicotinic acid (5.00 grams, 31.73 mmol) is then added portionwise over five minutes. When gas evolution subsides, the reaction is heated to reflux for 21 hours. It is then cooled to room temperature and 300 ml of water added. The aqueous layer is extracted with diethyl ether (3×200 ml), then pH adjusted to acidic with glacial acetic acid and stirred. After 2 hours, the precipitate which has formed is filtered and washed with (3×100 ml) water then (3×100 ml) pentane to yield 1.78 grams (19.8%) of product as a tan crystalline solid.

Workup

  1. customequipped with a stir bar and condenser under nitrogen
  2. additionDuring this addition
  3. temperatureWhen gas evolution subsides, the reaction is heated
  4. temperatureto reflux for 21 hours
  5. extractionThe aqueous layer is extracted with diethyl ether (3×200 ml)
  6. stirringstirred
  7. waitAfter 2 hours
  8. customthe precipitate which has formed
  9. filtrationis filtered
  10. washwashed with (3×100 ml) water

Sources & evidence

ORD record
ord-6d04672655484828a8fde85a07f825cf
Source dataset
uspto-grants-1989_08
Patent number
US04861891

Reaction notes

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