6(5H)-Phenanthridinone → 5-Cyclobutanecarbonyl-5H-phenanthridin-6-one

HRID 1178710Notes

Reaction equation

HRID 1178710 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.[CH:16]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17]1>>[CH:16]1([C:20]([N:6]2[C:7](=[O:15])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:21])[CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 18536(5H)-Phenanthridinone2×HCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 231186775-Cyclobutanecarbonyl-5H-phenanthridin-6-one

Procedure

5-Cyclobutanecarbonyl-5H-phenanthridin-6-one was prepared from 5H-phenanthridin-6-one and cyclobutanecarbonyl chloride according to GP 1. Yield, 2%. 1H-NMR (CD3OD): δ=1.95-2.09 (m, 1H), 2.11-2.26 (m, 1H), 2.36-2.55 (m, 4H), 3.64 (ψ-quint, J=8.5 Hz, 1H), 7.32 (“t”, J=7.5 Hz, 1H), 7.37 (“t”, J=7.7 Hz, 1H), 7.47 (“t”, J=7.5 Hz, 1H), 7.53 (“t”, J=7.5 Hz, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.5 Hz, 1H), 8.22 (d, J=7.7 Hz, 1H); (+)-ESI-MS: m/z=278 [M+H]+, 196 [5H-phenanthridin-6-one+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-ffbb69ee39344589bd1cafc4000cf589
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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