HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-[2-(Cyclobutylcarbonyl)aminophenyl]indoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclobutanecarbonyl chloride | HCID 78705 | — |
| Reactant | 2-(2,3-dihydro-1H-indol-1-yl)aniline hydrochloride | HCID 12519119 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[2-(Cyclobutylcarbonyl)aminophenyl]indoline | HCID 20376323 | — |
Reaction Steps
A slurry of 1-(2-aminophenyl)indoline hydrochloride (41.44 g) in CH2Cl2 (400 ml) under N2 at 0° C. is treated dropwise with a solution of triethylamine (2.2 equivalents) in CH2Cl2 (80 ml) and then with a solution of cyclobutylcarbonyl chloride (20 g) in CH2Cl2 (50 ml). After warming to room temperature, the product is poured into water (300 ml). The organic layer is washed with 4 N HCl, 2.5 N NaOH, water, dried (Na2SO4), filtered, and concentrated to yield 1-[2-(cyclobutylcarbonyl)aminophenyl]indoline, m.p. 81°-83.5° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04186199 |
| Source dataset | uspto-grants-1980_01 |
| ORD ID | ord-3af5af1cb54e4b099b99ccc5acaf017c |
| Source note | uspto-grants-1980_01 |