Sulfuric Acid → Methyl 4-(4-aminophenyl)-4-oxobutanoate

HRID 262917Notes

Reaction equation

HRID 262917 reaction equation
C([NH:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:7][CH:6]=1)(=O)C.S(=O)(=O)(O)O.[C:23]([O-])(=O)C.[Na+]>CO>[NH2:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([CH2:11][CH2:12][C:13]([O:15][CH3:23])=[O:14])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 2323374-(4-Acetamidophenyl)-4-oxobutanoic acidHCID 517045Sodium Acetate

Product 1

HCID 12016833Methyl 4-(4-aminophenyl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 35 g. of 3-p-acetamidobenzoylpropionic acid, 700 ml. of methanol and 1.4 ml. of concentrated sulfuric acid is refluxed for 76 hours. The solution is cooled to 35° C. and poured onto 7 g. of anhydrous sodium acetate while stirring. The reaction mixture is stirred in an ice-bath. The product is filtered and washed with cold methanol.

Workup

  1. additionA mixture of 35 g
  2. additionpoured onto 7 g
  3. filtrationThe product is filtered
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-a397ab3389eb43658d952e0a405cb63c
Source dataset
uspto-grants-1979_05
Patent number
US04154756

Reaction notes

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