Acetyl chloride → HCID 68954629, compound

HRID 750992Notes

Reaction equation

HRID 750992 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:10]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:27](Cl)(=O)C>CO>[OH:1][C:2]1[CH:3]=[C:4]([N:10]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([O:16][CH3:27])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10360501Benzoic acid, 3-[(3-hydroxy-4-methoxyphenyl)(3-pyridinylmethyl)amino]-

Product 1

HCID 68954629HCID 68954629, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(3-Hydroxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-3-aminobenzoic acid (7.0 g, 20.0 mmol) was dissolved in 210 mL of MeOH and 2.8 g (36.0 mmol) of acetyl chloride was added. The material was warmed to reflux with stirring overnight. The solution was concentrated in vacuo and then diluted with 200 mL of DCM and washed with saturated NaHCO3, brine, dried (Na2SO4), and concentrated to give 6.85 g (84% yield) of the desired target.

Workup

  1. temperatureThe material was warmed
  2. temperatureto reflux
  3. concentrationThe solution was concentrated in vacuo
  4. additiondiluted with 200 mL of DCM
  5. washwashed with saturated NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give 6.85 g (84% yield) of the desired target

Sources & evidence

ORD record
ord-7d7a9209c99543d7addca56ae8930622
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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