Methane → HCID 12833344, compound

HRID 1065287Notes

Reaction equation

HRID 1065287 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[OH-].[Na+].C>C(Cl)(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[N:2]([CH3:1])[C:3](=[O:20])[C:4]3[CH:9]=[CH:8][CH:7]=[N:6][C:5]=3[CH:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 12833329HCID 12833329, compound2×

Product 1

HCID 12833344HCID 12833344, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5 ml. of trifluromethanesulfonic acid were added to 4.6 g. (16.0 mmol.) of 2-(4'-chlorobenzoylmethyl)nicotinic acid N-methylamide (Compound XX) in 30 ml. chloroform stirred at 0° C. The resulting reaction mixture was then stirred at room temperature for 3 hours, chilled to 0° C. and made basic with 10% sodium hydroxide solution. Celite and charcoal were added and the entire reaction mixture was filtered through Celite. The phases were separated and the aqueous phase was extracted with methylene chloride. The organic phase and the methylene chloride extract were combined, dried over anhydrous magnesium sulfate and concentrated at reduced pressure to give the crude product as a light brown solid. The crude product was recrystallized from methylene chloride/diethyl ether and then from ethanol to give the product (2.5 g.), m.p. 139°-140° C.

Workup

  1. additionof trifluromethanesulfonic acid were added to 4.6 g
  2. customThe resulting reaction mixture
  3. temperaturechilled to 0° C.
  4. customthe entire reaction mixture
  5. filtrationwas filtered through Celite
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with methylene chloride
  8. extractionThe organic phase and the methylene chloride extract
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated at reduced pressure
  11. customto give the crude product as a light brown solid
  12. customThe crude product was recrystallized from methylene chloride/diethyl ether
  13. customfrom ethanol to give the product (2.5 g.), m.p. 139°-140° C.

Sources & evidence

ORD record
ord-6994a40004b14fd7bb732ccb6075b59b
Source dataset
uspto-grants-1982_05
Patent number
US04329349

Reaction notes

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