4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione → 10-Aminocamptothecin

HRID 2418791Notes

Reaction equation

HRID 2418791 reaction equation
[CH3:1][CH2:2][C:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=[CH:20]2)=[O:11]>C(O)C.O1CCOCC1.[Pt]=O>[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([NH2:26])[CH:21]=[CH:20]2)=[O:11]

Participants

5

Reactant 1

HCID 655674-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Product 1

HCID 10498610-AminocamptothecinYield 96.2%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

10-Nitrocamptothecin (108 mg, 0.275 m-mol) is dissolved in ethanol (30 ml) and dioxane (20 ml). To this solution is added platinum oxide (20 mg), and the mixture is subjected to catalytic reduction for 30 minutes at room temperature under normal pressure. The catalyst is removed by filtration and the reaction mixture is evaporated under reduced pressure until dryness whereby 96 mg (yield: 96.2%) of 10-aminocamptothecin is obtained as a yellowish brown solid.

Workup

  1. customThe catalyst is removed by filtration

Sources & evidence

ORD record
ord-1603585dc78d40eaa3545e33fc671fe4
Source dataset
uspto-grants-1984_09
Patent number
US04473692

Reaction notes

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