Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Ammonia → 6-Amino-3-hydroxy-2-phenyl-4H-chromen-4-one
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Ammonia | HCID 222 | — |
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Succinic anhydride | HCID 7922 | — |
| 반응물 | Succinamic acid | HCID 12522 | — |
| 반응물 | N-(3-hydroxy-4-oxo-2-phenyl-chromen-6-yl)acetamide | HCID 49864161 | — |
| 용매 | Ethanol | HCID 702 | — |
| 생성물 | 6-Amino-3-hydroxy-2-phenyl-4H-chromen-4-one | HCID 49864197 | — |
반응 단계
With substantial amounts of 4 in hand, the next steps were to form the 6-acetamidoflavonol. Thus, the acetophenone 4 was treated with benzaldehyde and base to effect a Claisen-Schmidt condensation affording the chalcone 5 in 71% yield. The chalcone 5 was treated with alkaline hydrogen peroxide to enable an Algar-Flynn-Oyamada reaction, giving 6-acetamidoflavonol 6 in 50% yield. The next step was to unveil the 6-amino group of 6 to allow coupling with succinic anhydride for installation of the succinamic acid side chain. The 6-acetamidoflavonol 6 was treated with 5 M HCl in ethanol at reflux, followed by neutralization with aqueous ammonia to give 6-aminoflavonol.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07863323B1 |
| 출처 데이터셋 | uspto-grants-2011_01 |
| ORD ID | ord-09f8c105d7134ada80c098906d1d2c90 |
| 출처 메모 | uspto-grants-2011_01 |