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

HRID 2181826Notes

Reaction equation

HRID 2181826 reaction equation
C[O:2][C:3]1[CH:16]=[C:15]2[C:6]([CH:7]([CH3:28])[N:8]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][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]([CH3:28])[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][CH:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823209-Methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 117264635-[(4-Hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-olYield 56%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 9-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.35 g, 0.89 mmol), tetrabutylammonium iodide (0.82 g, 2.2 mmol), and 1 M boron trichloride in dichloromethane (4.44 mL, 4.44 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), to yield 5-[(4-hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol as a solid (0.18 g, 56%), m.p. 212° C.;

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)

Sources & evidence

ORD record
ord-1b6f3752e19b4774a9c46b9473293ec5
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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