3-Aminophenol → 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide

HRID 1874592Notes

Reaction equation

HRID 1874592 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].[C:14]([C:16]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23])([CH3:18])[CH3:17])#[N:15]>O1CCCC1>[C:14]([C:16]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1)=[O:23])([CH3:18])[CH3:17])#[N:15]

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 573868253-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (10 g, 52.8 mmol) in tetrahydrofuran (100 mL) were added N,N-dimethylformamide (80 μL) and oxalyl chloride (6.28 mL, 72.0 mmol), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure to give 3-(cyano-1-methylethyl)benzoyl chloride as a pale-brown oil. To a solution of 3-aminophenol (5.24 g, 48.0 mmol) in tetrahydrofuran (40 mL) was added an aqueous suspension (60 mL) of sodium hydrogen carbonate (6.05 g, 72.0 mmol), and the mixture was vigorously stirred at room temperature. To this mixture was added dropwise a solution of 3-(cyano-1-methylethyl)benzoyl chloride in tetrahydrofuran (60 mL) synthesized above under ice-cooling, and the mixture was stirred at room temperature for 5 hr. The aqueous layer of the reaction mixture was separated, and the organic layer was diluted with ethyl acetate (200 mL) and washed with saturated brine (200 mL). The extract was dried over anhydrous magnesium sulfate and decolored with activated carbon. The insoluble material was filtered off through a pad packed with silica gel and celite in two layers. The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate-hexane mixture to give the title compound (13.03 g, 96%) as a colorless powder.

Workup

  1. customsynthesized above under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 5 hr
  4. customThe aqueous layer of the reaction mixture was separated
  5. additionthe organic layer was diluted with ethyl acetate (200 mL)
  6. washwashed with saturated brine (200 mL)
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off through a pad
  9. customThe solvent was evaporated under reduced pressure
  10. washthe obtained solid was washed with ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-b8f4772cc53343f595d5ec5f3c6eb91c
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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