Triethylamine → Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetate

HRID 1024424Notes

Reaction equation

HRID 1024424 reaction equation
CCN(CC)CC.Cl.[NH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:12].[CH2:22]([O:24][C:25](=[O:29])[C:26](Cl)=[O:27])[CH3:23]>CCOC(C)=O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11](=[O:12])[CH2:10][NH:9][C:26](=[O:27])[C:25]([O:24][CH2:22][CH3:23])=[O:29])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 27928012-Amino-1-(4-nitrophenyl)ethan-1-one hydrochloride

Product 1

HCID 66572182Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetateYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Et3N (8.88 ml) was added to a solution of 2-amino-1-(4-nitrophenyl)ethanone hydrochloride (step B product, 11.5 g) in EtOAc (115 ml). This was followed by drop wise addition of Ethylchlorooxoacetate (7.11 ml). The reaction mixture was refluxed for 2 hours. It was then cooled and quenched with water. The organic layer was separated, dried over Na2SO4 and the solvent was concentrated to get dark brown oil which was purified by column chromatography in 3:7 Ethyl acetate:Pet ether to get yellow solid. The solid was crystallized in ethyl acetate/pet ether to yield 8.9 g (59%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 9.21 (t, 1H), 8.35 (d, 2H), 8.24 (d, 2H), 4.78 (d, 2H), 4.29 (q, 2H), 1.29 (t, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperatureIt was then cooled
  3. customquenched with water
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationthe solvent was concentrated
  7. customto get dark brown oil which
  8. customwas purified by column chromatography in 3:7 Ethyl acetate
  9. customPet ether to get yellow solid
  10. customThe solid was crystallized in ethyl acetate/pet ether

Sources & evidence

ORD record
ord-7c302e5c456147f4a198f7dab5272abb
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

Loading…