4-Methylbenzoyl Chloride → 4-[4-(4-Methyl-benzoylamino)-phenyl]-4-oxo-butyric acid, methyl ester

HRID 1264091Notes

Reaction equation

HRID 1264091 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:17]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 12016833Methyl 4-(4-aminophenyl)-4-oxobutanoate

Product 1

HCID 120168344-[4-(4-Methyl-benzoylamino)-phenyl]-4-oxo-butyric acid, methyl esterYield 40.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-benzoyl chloride (0.74 mL, 0.0056 mol) and 4-(4-amino-phenyl)-4-oxo-butyric acid, methyl ester (0.93 g, 0.0045 mol) in toluene (22 mL) was refluxed under nitrogen for 17 hours and allowed to cool. The mixture was diluted with THF (20 mL), and washed with 0.1 M aqueous sodium hydroxide. The solids that remained undisolved were filtered, washed with water, and dried in house vacuum (40° C., air bleed) to give 0.592 g of 4-[4-(4methyl-benzoylamino)-phenyl]-4-oxo-butyric acid, methyl ester as an off-white solid; mp 192-195° C.

Workup

  1. temperaturewas refluxed under nitrogen for 17 hours
  2. temperatureto cool
  3. washwashed with 0.1 M aqueous sodium hydroxide
  4. filtrationThe solids that remained undisolved were filtered
  5. washwashed with water
  6. customdried in house vacuum (40° C., air bleed)

Sources & evidence

ORD record
ord-1b668bbccfab4481bc764fe8e7337da7
Source dataset
uspto-grants-2003_04
Patent number
US06541521B1

Reaction notes

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