Acetic Acid → HCID 12017609, compound

HRID 1279230Notes

Reaction equation

HRID 1279230 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=O)=[CH:4][CH:3]=1.[C-]#[N:20].[K+].[C:22]([OH:25])(=O)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2([C:22]([NH2:20])=[O:25])[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[C:14](=[O:15])[O:16]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 11254014HCID 11254014, compound

Product 1

HCID 12017609HCID 12017609, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-chlorobenzoyl)-2-pyridinecarboxylic acid (13 g), potassium cyanide (4.56 g), and acetic acid (30 mL) was heated at 120-125 C. in a sealed pressure bottle for 48 h. After cooling to ambient temperature, the mixture was poured into ice water. The precipitated solid was dissolved in ethyl acetate, washed with sodium bicarbonate saturated solution then with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was treated with ether. The formed solid was collected by filtration and dried to give 10.2 g of 5-(4-chlorophenyl)-7-oxo-5,7-dihydrofuro[3,4-b]pyridine-5-carboxamide. A mixture of 5-(4-chlorophenyl)-7-oxo-5,7-dihydrofuro[3,4-b]pyridine-5-carboxamide (5 g), 2-methyl-1,2-diamino propane (6.3 g), and toluene (80 mL) was heated at reflux for 18 h in a flask equipped with a water separator. The mixture was cooled to ambient temperature. The precipitated material was collected by filtration and dried to give the title compound (2.4 g), m.p. 257-260° C.

Workup

  1. temperaturewas heated at 120-125 C
  2. washwashed with sodium bicarbonate saturated solution
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. additionThe residue was treated with ether
  6. filtrationThe formed solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-c7fe61255f5349c98008343d53b75319
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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