Hydrochloric Acid → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-hydroxymethylphenyl)benzamide

HRID 323146

Reaction equation

HRID 323146 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](OCC)=[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.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>O1CCCC1>[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[CH2:30][OH: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 99135804-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-ethoxycarbonylphenyl)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 220107654-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-hydroxymethylphenyl)benzamideYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-ethoxycarbonylphenyl)benzamide (493 mg) in tetrahydrofuran (20 ml) was cooled in an ice bath. Lithium aluminum hydride (1M solution in tetrahydrofuran, 2.5 ml) was added dropwise to the solution and the mixture was stirred at the same temperature for 2 hours. Water was slowly added to the solution and resulting mixture was acidified with 1N hydrochloric acid. The solution was extracted with chloroform and the organic solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to silica gel column (20 g, 2% methanol in chloroform). The product was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-hydroxymethylphenyl)benzamide (245 mg) as a white powder.

Workup

  1. customresulting mixture
  2. extractionThe solution was extracted with chloroform
  3. washthe organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-deb1367bff014b7691c7277433338c96
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Linked notes

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