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

HRID 1105917Notes

Reaction equation

HRID 1105917 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-(4-acetamidobenzoyl)propionic 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 solid is collected and washed with cold methanol to yield methyl 3-(4-aminobenzoyl)propionate as a white solid. A mixture of this solid, 9.2 g. of 15-(trifluoromethyl)pentadecyl bromide and 4.2 g. of potassium carbonate is stirred for 20 hours at 125° C. under nitrogen. The mixture is then cooled to 25° C. and 30 ml. of water is added. After stirring, the product is filtered and washed with water. Recrystallization from methanol affords methyl 3-{4-[15-(trifluoromethyl)pentadecylamino]benzoyl}propionate as a white solid.

Workup

  1. additionA mixture of 35 g
  2. additionpoured onto 7 g
  3. customThe solid is collected
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-d19fb09d2b4b4cc485290b6ec7e18e06
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

Loading…