Dichloromethane → 5-[(4-Hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol

HRID 2181832Notes

Reaction equation

HRID 2181832 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH:5]([CH3:28])[N:6]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=12.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:6]2[CH:5]([CH3:28])[C:4]3[C:3]([OH:2])=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823397-Methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 104066525-[(4-Hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-olYield 61%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 7-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.17 g, 0.43 mmol), tetrabutylammonium iodide (0.39 g, 1.1 mmol), and 1 M boron trichloride in dichloromethane (2.6 mL, 2.6 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 (1:1), followed by trituration from dichloromethane, to yield 5-[(4-hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol as a homogenous solid (0.096 g, 61%);

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-b9b96b92b1ae4407a3ab199488e22fe2
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…