HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Anhydride → 1,3-dihydro-3-acetoxy-3-(2-pyridinylmethyl)-1-(4-morpholinyl)-2H-indol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 1,3-dihydro-3-hydroxy-1-(4-morpholinyl)-3-(2-pyridinyl methyl)-2H-indol-2-one | HCID 23353975 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1,3-dihydro-3-acetoxy-3-(2-pyridinylmethyl)-1-(4-morpholinyl)-2H-indol-2-one | HCID 23353981 | — |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
A mixture of alcohol from Example 26 (63 mg, 0.194 mmole) 4-dimethylaminopyridine (78 mg, 0.639 mmole), acetic anhydride (0.06 ml, 0.639 mmole) in dichloromethane (10 ml) was stirred at 0° C. for 8 hours. The volatiles were removed and the crude mixture applied directly to a silica gel column and eluted with 5% methanol in chloroform (Rf =0.34). The product slowly crystallized from hexane-ethyl acetate at 0° C. to give 41 mg of colorless cubes, m.p. 107°-110° C. after filtration. IR (KBr): 1702 cm-1. High Res. Mass Spec. Calcd. for C20H21N3O4 : 368.1610(M+H). Found: 368.1611.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05296478 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-a264f5572e5e45909ba7c38ea5ebfd47 |
| Source note | uspto-grants-1994_03 |