Water → Nicotinic Acid

HRID 964924Notes

Reaction equation

HRID 964924 reaction equation
Br.Br[CH2:3][CH2:4][CH2:5][NH2:6].[C:7](=[O:10])([O-])[O-:8].[K+].[K+].O.[C:14](OCC)(=O)[CH3:15].C1CCCCC1>C(Cl)Cl>[N:6]1[CH:15]=[CH:14][CH:3]=[C:4]([C:7]([OH:8])=[O:10])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 938Nicotinic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8.4 g (22.5 mmol) of acid chloride starting material used in Example 1 in 50 ml of methylene chloride were added 5.4 g of 3-bromopropylamine hydrobromide and 5.5 g of potassium carbonate. The mixture was stirred at room temperature for one hour and then 20 ml of water was added. Stirring was continued for 18 hours. After that the organic layer was separated, washed with brine and concentrated. The oily residue was triturated with cyclohexane to give a solid. A 2.3 g analytically pure sample was obtained by chromatography of 2.6 g of crude 3-pyridinecarboxylic acid, 5-[[(3-bromopropyl)amino]carbonyl]-6-(difluoromethyl)-4-(2-methylpropyl)-2-(trifluoromethyl)-, methyl ester on silica gel columns with 20% ethyl acetate/cyclohexane as eluting solvent, m.p. 107°-110° C.

Workup

  1. stirringStirring
  2. waitwas continued for 18 hours
  3. customAfter that the organic layer was separated
  4. washwashed with brine
  5. concentrationconcentrated
  6. customThe oily residue was triturated with cyclohexane
  7. customto give a solid

Sources & evidence

ORD record
ord-72acc8aa374541b79ad2c9643f68af87
Source dataset
uspto-grants-1998_06
Patent number
US05773389

Reaction notes

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