Dichloromethane → 5-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol

HRID 2181828Notes

Reaction equation

HRID 2181828 reaction equation
C[O:2][C:3]1[CH:16]=[C:15]2[C:6]([CH:7]([CH3:29])[N:8]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([CH3:28])[CH:21]=3)(=[O:19])=[O:18])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:8]2[CH:7]([CH3:29])[C:6]3[C:15](=[CH:16][C:3]([OH:2])=[CH:4][CH:5]=3)[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)(=[O:19])=[O:18])=[CH:21][C:22]=1[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224822639-Methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 99998865-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-olYield 40%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 9-methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.27 g, 0.66 mmol), tetrabutylammonium iodide (0.61 g, 1.7 mmol), and 1 M boron trichloride in dichloromethane (3.3 mL, 3.3 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane, to yield 5-[(4-hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol as a homogeneous solid (0.10 g, 40%);

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

Sources & evidence

ORD record
ord-c4a7df42708845cab072c7f194cb1ad4
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…