Nitric Acid → 12-Nitrocamptothecin

HRID 1840684Notes

Reaction equation

HRID 1840684 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[N+:27]([O-])([OH:29])=[O:28]>S(=O)(=O)(O)O>[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:20]([N+:27]([O-:29])=[O:28])=[CH:19][CH:18]=[CH:17][C:16]2=[CH:15][C:14]=1[CH2:13]3)=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 24360Camptothecin

Product 1

HCID 1101470512-Nitrocamptothecin

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Japanese Kokai Patent Application No. 59-51288 provides one method of making 9-nitro-camptothecin by treating camptothecin with a slight excess of concentrated nitric acid in concentrated sulfuric acid. However, when following this procedure, a yield of about 3% to about 7% of the 9NC product which is capable for medicinal use is obtained. Further, this procedure results in unwanted byproducts such as the inactive isomer, 12-nitrocamptothecin (12NC), in a ratio of about 1 to 3 of 9NC to 12NC. The following scheme shows the reaction from the use of nitric acid and sulfuric acid.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-110182070bf74ebfaaf26d3674b6c2f1
Source dataset
uspto-grants-2004_01
Patent number
USRE038408E1

Reaction notes

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