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

HRID 252234Notes

Reaction equation

HRID 252234 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-e6c54fb2f43e478bbb9c05eff783b057
Source dataset
uspto-grants-2011_01
Patent number
US07868033B2

Reaction notes

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