Ethyl Acetate → 2-(4-tert-butylbenzoylamino)-5-amino-N-(4-methoxyphenyl)benzamide

HRID 427567Notes

Reaction equation

HRID 427567 reaction equation
[C:1]([C:5]1[CH:33]=[CH:32][C:8]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>C(O)C.[Pd]>[C:1]([C:5]1[CH:33]=[CH:32][C:8]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 106710992-(4-Tert-butylbenzoylamino)-5-nitro-n-(4-methoxyphenyl)benzamide

Product 1

HCID 106456292-(4-tert-butylbenzoylamino)-5-amino-N-(4-methoxyphenyl)benzamideYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(4-tert-butylbenzoylamino)-5-nitro-N-(4-methoxyphenyl)benzamide (895 mg, 2.00 mmol), 10% palladium-on-carbon (90 mg) and ethyl acetate (5 ml) in ethanol (5 mL) was hydrogenated at one atmospheric pressure for 5 h. The reaction was degassed and a suspension of 10% palladium-on-carbon (45 mg) and ethyl acetate (3 mL) was added. This mixture was hydrogenated for 2 days at one atmosphere. The reaction was filtered through diatomaceous earth assisted by ethyl acetate/ethanol washes. The filtrate was concentrated in vacuo and chromatographed (silica gel, 10% ethyl acetate/90% methylene chloride to 35% ethyl acetate/65% methylene chloride) to give 487 mg (58%) of the title compound as a white solid; mp 212-214.5° C.

Workup

  1. customThe reaction was degassed
  2. additiona suspension of 10% palladium-on-carbon (45 mg) and ethyl acetate (3 mL)
  3. additionwas added
  4. waitThis mixture was hydrogenated for 2 days at one atmosphere
  5. filtrationThe reaction was filtered through diatomaceous earth
  6. concentrationThe filtrate was concentrated in vacuo
  7. customchromatographed (silica gel, 10% ethyl acetate/90% methylene chloride to 35% ethyl acetate/65% methylene chloride)

Sources & evidence

ORD record
ord-29d06cf1ec4d428fad9dbb5a17c06524
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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