HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Bromide → HCID 8166485, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Chloro-2-hydroxybenzamide | HCID 348094 | — |
| Reactant | 5-chloro-2-(aminocarbonylmethyloxy)benzylamine | HCID 11183494 | — |
| Reactant | HCID 11436574 | HCID 11436574 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 8166485 | HCID 8166485 | 98% |
Reaction Steps
Compounds 72 and 73 were synthesized through a Sonogashira-type reaction in high yield using CuI and (Ph3P)PdCl2 as catalysts. Sonogashira et al., Tet. Lett. 1975, 4467-4470. For the preparation of both 5-chloro-2-benzyloxybenzylamine 76 and 5-chloro-2-(aminocarbonylmethyloxy)benzylamine 80, 5-chloro-2-hydroxybenzamide 74 was used as starting material. Compound 74 was treated with benzyl bromide in the presence of K2CO3 in N,N-dimethylformamide to obtain 5-chloro-2-benzyloxybenzamide 75 in 98% yield. Finally, the amide 75 was reduced to the corresponding amine 76 with LiAlH4 in tetrahydrofuran.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07825126B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-2c873a37e9b54f529841cddf5b82f040 |
| Source note | uspto-grants-2010_11 |