Benzamide, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)- → HCID 15389740, compound

HRID 2373729Notes

Reaction equation

HRID 2373729 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)=[O:9])([CH3:4])[CH3:3].[H][H]>C(O)C.ClCCl.[Pd]>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:9])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 7124367Benzamide, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 15389740HCID 15389740, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

In a 250 ml Parr flask, 2.4 g (6.5 mmoles) of 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-benzamide is dissolved in 50 ml of an absolute ethanol/dichloromethane mixture (1/1) in the presence of 10% Pd/C. The mixture is agitated under 20 PSI of hydrogen, at 30° C., for one hour. After filtration on celite, the filtrate is concentrated under vacuum. The evaporation residue is taken up in 25 ml of a 1M HCl solution. The precipitate formed is filtered and rinsed with 50 ml of diethyl ether followed by 50 ml of ethyl acetate. The amine is released from its salt by agitation in a mixture of 50 ml of ethyl acetate and 50 ml of 1M NaOH. After decanting, the organic phase is washed with 25 ml of 1M NaOH and 25 ml of brine. The organic solution is dried over sodium sulphate, filtered, rinsed and concentrated to dryness under reduced pressure to produce 1.09 g (49%) of a white powder. Melting point: 220-221° C.

Workup

  1. filtrationAfter filtration on celite
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washrinsed with 50 ml of diethyl ether
  6. additionThe amine is released from its salt by agitation in a mixture of 50 ml of ethyl acetate and 50 ml of 1M NaOH
  7. customAfter decanting
  8. washthe organic phase is washed with 25 ml of 1M NaOH and 25 ml of brine
  9. dry with materialThe organic solution is dried over sodium sulphate
  10. filtrationfiltered
  11. washrinsed
  12. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-347f8cb228f1416fa23caf49c9a611a1
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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