Ammonia → HCID 19348480, compound

HRID 1637509Notes

Reaction equation

HRID 1637509 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].[NH3:17].C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C.CCCCCC>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](=[O:10])[NH2:17])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8058HexaneHCID 8857Ethyl AcetateHCID 7388134-Tert-butyl-3-nitrobenzoic acid

Product 1

HCID 19348480HCID 19348480, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

12.0 g (74.0 mmol) of N,N'-carbonyldiimidazole were added to a suspension of 15.03 g (67.3 mmol) of 4-t-butyl-3-nitrobenzoic acid in 150 ml of acetonitrile, and the resulting mixture was stirred for 1 hour, after which 20 ml (0.31 mol) of aqueous ammonia were added. The reaction mixture was stirred for 30 minutes, after which it was concentrated by evaporation under reduced pressure, and the concentrate was dissolved in ethyl acetate. The organic phase was washed with water, with 2 N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 150 g of silica gel, using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:1 to 2:1 by volume as the eluent, to give 12.68 g (yield 85%) of the title compound as crystals, melting at 114-115° C. (from ethyl acetate-hexane).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. concentrationafter which it was concentrated by evaporation under reduced pressure
  3. dissolutionthe concentrate was dissolved in ethyl acetate
  4. washThe organic phase was washed with water, with 2 N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 150 g of silica gel
  8. washa gradient elution method

Sources & evidence

ORD record
ord-4b4e4b1d1a714ea1b03faa32d6f1446e
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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