Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | Cesium iodide | HCID 24601 | — |
| 반응물 | 2-Bromo-1,1-dimethoxyethane | HCID 81672 | — |
| 반응물 | 6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one | HCID 15908314 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline | HCID 18963883 | — |
반응 단계
6-Hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline is treated with bromacetaldehyde dimethyl acetal, in the presence of Cs2CO3 and CsI in DMF to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline. Treatment with 2-chloromethylpyridine hydrochloride in the presence of sodium hydride in DMF yields 6-(2,2-dimethoxyethoxy)2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline. Hydrolysis with 20% aqueous sulfuric acid in THF yields α-[2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yloxy]-acetaldehyde which is then converted to 2-(2-pyridylmethyl)-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05260316 |
| 출처 데이터셋 | uspto-grants-1993_11 |
| ORD ID | ord-ebf4cc4857a445ca810ceabd00a34116 |
| 출처 메모 | uspto-grants-1993_11 |