Pyridine → Methyl 4-acetamidosalicylate

HRID 1722647Notes

Reaction equation

HRID 1722647 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl.O>[C:19]([NH:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 77787Methyl p-aminosalicylate

Product 1

HCID 77719Methyl 4-acetamidosalicylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10 g (59.9 mmol) of methyl 4-aminosalicylate in 100 ml of CH2Cl2 is added 6.8 ml (83.9 mmol) of pyridine in one portion at room temperature. The solution is cooled to 0° C. and 4.7 ml (65.9 mmol) of acetyl chloride is added dropwise. After addition is complete the reaction mixture is let stand 30 minutes at room temperature. The reaction mixture is diluted with water and extracted with CH2Cl2. The combined organic extracts are dried over MgSO4, filtered and concentrated to provide methyl 4-acetylaminosalicylate which is used directly in the next step.

Workup

  1. additionAfter addition
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-661ae851518d4155bcb20c28d6184099
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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