HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Chloroaniline → HCID 22313565, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Chloroaniline | HCID 7812 | — |
| Reactant | 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester | HCID 379000 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 22313565 | HCID 22313565 | 94.3% |
Reaction Steps
Tert butyl-2-oxo-1-pyrrolidinecarboxylate (190 mg, 1.02 mmol), 4-chloroaniline (64 mg, 0.5 mmol) and acetic acid (184 mg) were mixed in dichloroethane (5 mL). Sodium triacetoxyborohydride (326.5 mg) was added and the reaction mixture kept on stirring at room temperature for overnight. After addition of aq. NaHCO3 the reaction mixture was diluted by addition of ethyl acetate. Two layers were separated. The organic layer was dried over Na2SO4, filtered, concentrated. The residue was purified by flash chromatography (0-15% ethyl acetate in petroleum spirit, 40-60) to give the subtitled product (140 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06927222B2 |
| Source dataset | uspto-grants-2005_08 |
| ORD ID | ord-2e6859bb30924dde8da38b9af94dc9a0 |
| Source note | uspto-grants-2005_08 |