4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-ethoxycarbonylphenyl)benzamide → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxyphenyl)benzamide

HRID 323139Notes

Reaction equation

HRID 323139 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([O:32]CC)=[O:31])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([OH:32])=[O:31])=[O:22])=[CH:36][CH:37]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 99135804-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-ethoxycarbonylphenyl)benzamide

Product 1

HCID 220109694-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxyphenyl)benzamideYield 92.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-ethoxycarbonylphenyl)benzamide (500 mg) in a mixture of ethanol (20 ml) and 1N sodium hydroxide (2 ml) was heated at reflux for 4 hours and ethanol was evaporated in vacuo. Water (5 ml) was added to the residue and the aqueous solution was adjusted to pH 2 with 1N hydrochloric acid. The precipitate was filtered to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxyphenyl)benzamide (435 mg) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customethanol was evaporated in vacuo
  4. additionWater (5 ml) was added to the residue
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-7081f0a99bec448296284ccaa9c42242
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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