6(5H)-Phenanthridinone → 5-(Furan-2-carbonyl)-5H-phenanthridin-6-one

HRID 1178711Notes

Reaction equation

HRID 1178711 reaction equation
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21](Cl)=[O:22]>>[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([N:6]1[C:7](=[O:15])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:22]

Participants

3

Reactant 2

HCID 18536(5H)-PhenanthridinoneHCID 682422-Furancarbonyl chloride

Product 1

HCID 231186855-(Furan-2-carbonyl)-5H-phenanthridin-6-one

Procedure

5-(Furan-2-carbonyl)-5H-phenanthridin-6-one was prepared from 5H-phenanthridin-6-one and 2-furoyl chloride according to GP 1. Yield, 2%. 1H-NMR (CD3OD): δ=6.77 (dd, J=3.6 Hz, J=1.8 Hz, 1H), 7.44 (ddd, J=J=7.5 Hz, J=1.0 Hz, 1H), 7.41 (ddd, J=J=7.7 Hz, J=1.1 Hz, 1H), 7.48 (ddd, J=J=7.5 Hz, J=1.1 Hz, 1H), 7.54 (ddd, J=J=7.5 Hz, J=1.1 Hz, 1H), 7.57 (dd, J=3.6 Hz, J=0.7 Hz, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.92 (d, J=7.5 Hz, 1H), 7.95 (dd, J=1.8 Hz, J=0.7 Hz, 1H), 8.47 (d, J=7.7 Hz, 1H); (+)-ESI-MS: m/z=290 [M+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-6b459fa1c7b547ac8409b07fb3583e79
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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