Triethylamine → 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623771Notes

Reaction equation

HRID 1623771 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([CH:16]=1)[C:13]([OH:15])=O.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=1.C(N(CC)CC)C>ClCCl>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([CH:16]=1)[C:13]([NH:31][C:27]1[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 247719442-(Benzyloxy)-5-hydroxybenzoic acid

Product 1

HCID 513575145-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1.08 ml, 12.28 mmol) was added to a mixture of 5-hydroxy-2-[(phenylmethyl)oxy]benzoic acid (1 g, 4.09 mmol) dissolved in dichloromethane. The mixture was stirred for 2 h, and then concentrated. The residue was dissolved in dichloromethane, and then added to a mixture of pyridin-3-amine (0.39 g, 4.09 mmol) and triethylamine (1.14 ml, 8.19 mmol) in dichloromethane. The mixture was stirred at 40° C. for 3 h. The mixture was filtered, and the filtrate was added to water (10 ml) and extracted with ethyl acetate (30 ml). The organic phase was concentrated to yield the title compound as a crude solid product. 0.72 g.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. stirringThe mixture was stirred at 40° C. for 3 h
  4. filtrationThe mixture was filtered
  5. additionthe filtrate was added to water (10 ml)
  6. extractionextracted with ethyl acetate (30 ml)
  7. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-a8fc597cb15046aeb2447e30592cd120
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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