Pyridine → Methyl 4-(6-acetamido-2-methylpyridin-3-yl)benzoate

HRID 2214755Notes

Reaction equation

HRID 2214755 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl>[C:25]([NH:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 21948386HCID 21948386, compound

Product 1

HCID 11173633Methyl 4-(6-acetamido-2-methylpyridin-3-yl)benzoateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of methyl 4-(6-amino-2-methylpyridin-3-yl)benzoate (Description 7 in EP 97/17351, 300 mg, 1.2 mmole) and pyridine (0.16 ml, 2.0 mmole) in DCM (35 ml) at 0° C. under argon was treated with acetyl chloride (120 mg, 1.5 mmole) and allowed to warm to room temperature over 1 h. Additional acetyl chloride (120 mg) was added, the mixture maintained at room temperature for a further 1 h, then washed with 10% Na2CO3 solution, dried (Na2SO4) and concentrated under vacuum to afford the title compound as a white solid (344 mg, 98%).

Workup

  1. temperaturethe mixture maintained at room temperature for a further 1 h
  2. washwashed with 10% Na2CO3 solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-11a9e70e5d1d4fe187432600ed074ebe
Source dataset
uspto-grants-2006_09
Patent number
US07109201B2

Reaction notes

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