Pyridine → 4-(4-Cyano-benzoylamino)-3-hydroxy-benzoic acid

HRID 2196476Notes

Reaction equation

HRID 2196476 reaction equation
NC1C=C(C=CC=1O)[C:5]([OH:7])=[O:6].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)#[N:19].C1C[O:32][CH2:31]C1>>[C:18]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:12][C:17]2[CH:16]=[CH:15][C:14]([C:5]([OH:7])=[O:6])=[CH:13][C:31]=2[OH:32])=[O:25])=[CH:22][CH:21]=1)#[N:19]

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 650833-Amino-4-hydroxybenzoic acidHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 608268404-(4-Cyano-benzoylamino)-3-hydroxy-benzoic acid

Procedure

To a stirred solution of 3-Amino-4-hydroxy benzoic acid (0.185 g, 0.0012 mols) and pyridine (0.287 g, 0.00363 mols) in 18.5 ml dry THF is added 4-cyanobenzoyl chloride (0.2 g, 0.0012 mols) and the solution is stirred under nitrogen atmosphere at RT for 10 hrs and then refluxed for 3 hrs. The reaction mixture is rotary evaporated and the residue is slurried in water and filtered to get the amide (0.18 g) which is taken for the next step without further purification.

Workup

  1. temperaturerefluxed for 3 hrs
  2. customThe reaction mixture is rotary evaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1dfc829375854ee4a448d73bfa7b01c3
Source dataset
uspto-grants-2012_12
Patent number
US08338459B2

Reaction notes

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