HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6'-(2-Methyl-5-(1,3,4-oxadiazol-2-yl)phenyl)spiro[cyclopentane-1,3'-indolin]-2'-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethyl orthoformate | HCID 9005 | — |
| Reactant | 4-Methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzohydrazide | HCID 58170462 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | 6'-(2-Methyl-5-(1,3,4-oxadiazol-2-yl)phenyl)spiro[cyclopentane-1,3'-indolin]-2'-one | HCID 44250818 | 60.3% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A stirred mixture of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzohydrazide (preparation 53, 0.16 g, 0.24 mmol) and trimethylorthoformate (0.24 mL, 1.44 mmol) in acetic acid (3 mL) were heated to 150° C. in a sealed tube. After 3 hours, the mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and evaporated in vacuo. Purification of the residue by flash chromatography (1:1 hexanes/ethyl acetate) gave the title compound (0.05 g, 60%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772288B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-6d337581212d468ea1c8b5354951c013 |
| Source note | uspto-grants-2014_07 |