Hydrochloric Acid → 4-(2-Pyridyl)Benzoic Acid

HRID 1859883Notes

Reaction equation

HRID 1859883 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:28].C(P(=O)(OCC)O[CH2:33][CH3:34])#N.C([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])C>O1CCOCC1.CN(C)C=O>[ClH:28].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1.[N:41]1[CH:42]=[CH:43][CH:34]=[CH:33][C:44]=1[C:45]1[CH:26]=[CH:25][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 18625963HCID 18625963, compound

Product 2

HCID 8216924-(2-Pyridyl)Benzoic AcidHCID 18625894HCID 18625894, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-propylpropionate (2.20 g) in dioxane containing hydrogen chloride (4N, 30 ml) was allowed to stand at ambient temperature for 40 minutes. At the end of this time the reaction mixture was concentrated under reduced pressure and the hydrogen chloride was azeotropically distilled off with toluene to give a residue. A solution of diethyl cyanophosphonate (0.97 ml) in N,N-dimethylformamide (4.0 ml) was added to a solution of the residue obtained above (ethyl 3-[4-(2-aminoethoxy)phenyl]-2-propylpropionate hydrochloride), 4-pyridine-2-ylbenzoic acid (1.21 g) and triethylamine (1.80 ml) in N,N-dimethylformamide (8.0 ml) in an ice bath. The mixture was stirred for 1 hour in an ice bath and for 3 hours at ambient temperature. The reaction mixture was partitioned between ethyl acetate and water and the ethyl acetate was separated and washed with saturated aqueous sodium hydrogencarbonate and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using dichloroethane/ethyl acetate=7/3 as the eluant to give the title compound (2.20 g) as a pale yellow powder.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated under reduced pressure
  2. distillationthe hydrogen chloride was azeotropically distilled off with toluene
  3. customto give a residue

Sources & evidence

ORD record
ord-5b8e8d82f3c542b68fcbb215e80ed65c
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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