Ammonium Chloride → 6(5h)-Phenanthridinone, 2-amino-

HRID 1016483Notes

Reaction equation

HRID 1016483 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1)([O-])=O.[Cl-].[NH4+]>CN(C=O)C.[Fe]>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 1571802-Nitro-6(5H)-phenanthridinone

Product 1

HCID 2706686(5h)-Phenanthridinone, 2-amino-

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-nitro-6(5H)-phenanthridinone in DMF was reduced by iron and ammonium chloride to produce 2-amino-6(5H)-phenanthridinone. Chloroacylation of 2-amino-6(5H)-phenanthridinone with chloroacetyl chloride in pyridine/DMF yielded N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide, which then was treated with dimethyl amine in methanol or with N,N-dimethylformamide to furnish the N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-N,N-dimethylacetamide. This latter compound was then treated with HCl in ether in presence of methanol to give PJ34 as a water-soluble HCl salt. Product identity and purity were assessed using 1HNMR, MS, TLC and HPLC.

Sources & evidence

ORD record
ord-cca978dfd02c4c56a769b39e5c814d68
Source dataset
uspto-grants-2002_11
Patent number
US06476048B1

Reaction notes

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