Phenanthridine → 6-Ethyl-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine

HRID 2181802Notes

Reaction equation

HRID 2181802 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.[CH2:15]([Li])[CH3:16].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][C:21]=1[CH3:30]>C(OCC)C>[CH2:15]([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[S:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[C:21]([CH3:30])[CH:22]=1)(=[O:28])=[O:27])[CH3:16]

Participants

5

Reactant 3

HCID 9189PhenanthridineHCID 159153174-Methoxy-3-methylbenzene-1-sulfonyl chlorideHCID 178506846HCID 178506846, compound

Product 1

HCID 224823036-Ethyl-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared from phenanthridine, 0.62 M ethyllithium in diethyl ether, and 4-methoxy-3-methylbenzenesulfonyl chloride according to the procedure and in the same manner as described in Example 18, step a and yielded, after chromatographic purification and crystallization from diethyl ether, 6-ethyl-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine as a colorless, crystalline, solid, which was characterized by LCMS (ES+, FA, CV=5) and 1H NMR.

Workup

  1. customyielded
  2. customafter chromatographic purification and crystallization from diethyl ether, 6-ethyl-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine as a colorless, crystalline, solid, which

Sources & evidence

ORD record
ord-153821531fad4615bdbcd4b432500841
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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