Sulfuric Acid → HCID 90417884, compound

HRID 588263Notes

Reaction equation

HRID 588263 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([OH:13])=O)[CH:8]=2)[NH:3]1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:34][CH2:35][C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=O.S(=O)(=O)(O)O>CN(C=O)C.CCOC(C)=O.O>[C:38]1([C:36]2[O:13][C:11]([C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:10]4)=[N:34][CH:35]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 90417884HCID 90417884, compoundYield 13.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-oxoindoline-5-carboxylic acid (1.3 g, 7.3 mmol) in DMF (50 ml) was added iPr2NEt (3.8 ml, 22 mmol), HOBt (1.2 g, 8.8 mmol), WSCI (1.7 g, 8.8 mmol) and 2-amino-1-phenylethanone hydrochloride (1.3 g, 7.3 mmol). The reaction mixture was stirred for 2 h at room temperature. The mixture was poured into H2O and EtOAc. The resulting precipitate was removed by filtration, and the filtrate was separated. The organic layer was washed with sat. NaHCO3 solution, sat. NH4Cl solution and brine, and then dried over Na2SO4. The solvent was evaporated and the residue (0.73 g) was used for the next reaction without further purification. Sulfuric acid (5 ml) was added to the residue, and the mixture was heated for 2 h at 100° C. Ice was added, and the mixture was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated. The residue was crystallized from EtOH to afford 5-(5-phenyloxazol-2-yl)indolin-2-one (0.27 g, 13%).

Workup

  1. customThe resulting precipitate was removed by filtration
  2. customthe filtrate was separated
  3. washThe organic layer was washed with sat. NaHCO3 solution, sat. NH4Cl solution and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue (0.73 g) was used for the next reaction without further purification
  7. temperaturethe mixture was heated for 2 h at 100° C
  8. additionIce was added
  9. extractionthe mixture was extracted with EtOAc
  10. washThe organic layer was washed with H2O and brine
  11. dry with materialdried over Na2SO4
  12. customevaporated
  13. customThe residue was crystallized from EtOH

Sources & evidence

ORD record
ord-fd7e27f90f414632978fd575dfc3f78b
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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