Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Chloro-5-nitrobenzaldehyde | HCID 72933 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 43091262 | HCID 43091262 | 81.2% |
Reaction Steps
2-chloro-5-nitrobenzaldehyde (1 g, 5.39 mmol) was dissolved in THF (10 mL), and added with dimethylamine (2 M THF solution, 2.7 mL, 5.39 mmol). The reaction solution was cooled to 0° C., and NaBH(OAc)3 (1.6 g, 7.55 mmol) was slowly added thereto, followed by stirring for 12 hours or more at room temperature. The reaction mixture was added with water, and subjected to extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (940 mg, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09156852B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-ed2cdb6902f4418c9ccd72b2838342ec |
|---|
| Source note | uspto-grants-2015_10 |
|---|