Acetyl chloride → HCID 23118687, compound

HRID 1178747Notes

Reaction equation

HRID 1178747 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:17])[CH3:16].C[Si](C)(C)[O:21][C:22]1[CH2:26][CH2:25][CH2:24][CH:23]=1>>[C:15]([N:6]1[CH:7]([CH:23]2[CH2:24][CH2:25][CH2:26][C:22]2=[O:21])[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:17])[CH3:16]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 9189PhenanthridineHCID 88326Cyclopentene, 1-[(trimethylsilyl)oxy]-

Product 1

HCID 23118687HCID 23118687, compound

Procedure

2-(5-Acetyl-5,6-dihydro-phenanthridin-6-yl)-cyclopentanone was prepared from phenanthridine, acetyl chloride, and 1-(trimethylsilyloxy)cyclopentene according to GP 2. Yield, 25%. 1H-NMR (DMSO-d6): δ=1.23-1.38 (m, 2H), 1.43-1.61 (m, 1H), 1.67-1.81 (m, 1H), 1.81-2.27 (m, 6H), 6.15 (s, 1H), 7.21-7.56 (m, 6H), 7.85-7.97 (m, 2H); (+)-ESI-MS: m/z=306 [M+H]+, 222, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-025fb13f834b40d59a019837abaf9b4c
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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