Acetyl chloride → HCID 68489381, compound

HRID 1178748Notes

Reaction equation

HRID 1178748 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].[Si]([O:26][C:27]([O:29][CH3:30])=[CH2:28])(C(C)(C)C)(C)C>>[CH3:30][O:29][C:27](=[O:26])[CH2:28][CH:7]1[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]=2[N:6]1[C:15](=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 9189PhenanthridineHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyethene

Product 1

HCID 68489381HCID 68489381, compound

Procedure

(5-Acetyl-5,6-dihydro-phenanthridin-6-yl)-acetic acid methyl ester was prepared from phenanthridine, acetyl chloride, and 1-(tert-butyldimethylsilyloxy)-1-methoxyethene according to GP 2. Yield, 43%. 1H-NMR (DMSO-d6): δ=2.12 (s, br., 3H), 2.28-2.43 (m, 2H), 3.54 (s, 3H), 6.22 (s, br., 1H), 7.28-7.56 (m, 6H), 7.90-7.98 (m, 2H); (+)-ESI-MS: m/z=296 [M+H]+, 254, 222, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-627a903f14cb4e5cb6c8da87e3245c0d
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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