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

HRID 1168469Notes

Reaction equation

HRID 1168469 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-(4-methyl-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-9c494e0b984b4fcca8b7a5b77d7fad37
Source dataset
uspto-grants-2003_09
Patent number
US06624196B2

Reaction notes

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