Pyridine → 4-Benzamido-3-hydroxybenzoic acid

HRID 1481689Notes

Reaction equation

HRID 1481689 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:18]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 608270074-Benzamido-3-hydroxybenzoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-amino-3-hydroxybenzoic acid (7.66 g, 50.0 mmol) in THF (100 mL) was added pyridine (4.3 mL, 53.2 mmol, 1.06 eq) followed by benzoyl chloride (6.1 mL, 52.6 mmol, 1.05 eq) at 0° C. After 5 min, the reaction was quenched with H2O then extracted with CH2Cl2 (4×80 mL). Crude product precipitated out of organic layer then was collected by filtration to afford 4-benzamido-3-hydroxybenzoic acid (10.1 g, 39.3 mmol, 79%). The product was carried over to next step without further purification.

Workup

  1. customthe reaction was quenched with H2O
  2. extractionthen extracted with CH2Cl2 (4×80 mL)
  3. customCrude product precipitated out of organic layer
  4. filtrationthen was collected by filtration

Sources & evidence

ORD record
ord-6f0b82c20ed04ae6a441016724312b11
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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