2-Acetyl-3-pyridinecarboxylic acid → HCID 178467407, compound

HRID 2372206Notes

Reaction equation

HRID 2372206 reaction equation
[C:1]([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)(=[O:3])[CH3:2].[F:13][C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:25])[NH:23][NH2:24])[CH:17]=[C:18]([F:20])[CH:19]=1>CO>[F:13][C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:25])[NH:23][N:24]=[C:6]([OH:8])[C:5]2[CH:9]=[CH:10][CH:11]=[N:12][C:4]=2[C:1](=[O:3])[CH3:2])[CH:17]=[C:18]([F:20])[CH:19]=1

Participants

4

Reactant 2

HCID 101762782-Acetyl-3-pyridinecarboxylic acidHCID 152786873-Amino-1-(3,5-difluorophenyl)urea

Product 1

HCID 178467407HCID 178467407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 mg of 2-acetylnicotinic acid are added 56 mg of 4-(3,5-difluorophenyl)semicarbazide and 1 mL of methanol. After a minute of stirring the product begins precipitating from the solution. After stirring overnight (15 h) the stir vane is removed and rinsed with 0.2 mL of methanol. The reaction mixture is centrifuged and the supernatant solution removed. In the same way the solid is rinsed with methanol (3×0.5 mL) and ether (1×0.5 mL). The solid is dried in vacuo with heating to give 2-acetylnicotinic acid 4-(3,5-difluorophenyl)semicarbazone (also known as 2-[methyl-{[(3,5-difluorophenylamino)carbonyl]hydrazono}methyl]-3-pyridine-carboxylic acid), m.p. 186° (compound 31, Table A).

Workup

  1. custombegins precipitating from the solution
  2. stirringAfter stirring overnight (15 h) the stir vane
  3. customis removed
  4. washrinsed with 0.2 mL of methanol
  5. customthe supernatant solution removed
  6. washIn the same way the solid is rinsed with methanol (3×0.5 mL) and ether (1×0.5 mL)
  7. customThe solid is dried in vacuo
  8. temperaturewith heating

Sources & evidence

ORD record
ord-6f8d91d8f9574f7385d242225ff1c001
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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