Hydroxide → 2-Phenanthridinol, 7,8,9,10-tetrahydro-

HRID 1198801Notes

Reaction equation

HRID 1198801 reaction equation
C([O:4][C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][N:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:6]=1)(=O)C.[OH-]>CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[OH:4][C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][N:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:6]=1

Participants

6

Reactant 2

HCID 961HydroxideHCID 15678068HCID 15678068, compound

Product 1

HCID 110743862-Phenanthridinol, 7,8,9,10-tetrahydro-Yield 98%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Compound 274 (26.50 g, 110 mmol) in dry methanol (150 mL) was added Dowex 1x8-200 hydroxide form (0.40 g, catalytic), and tetra-n-butylammonium bromide (50 mg, catalytic), and the resulting mixutre was stirred at 60° C. for 24 hours. The reaction mixture was cooled, diluted with ethyl ether (100 mL) and filtered to give 21.47 g (98 percent) of Compound 275: white crystalline solid; mp 284°-286° C. (dec.); Rf =0.25 (silica, 50 percent ethyl acetate in dichloromethane); IR (CHCl3) νmax 2933, 2906, 2850, 2582, 1627, 1503, 1421 cm-1 ; 1H NMR (500 MHz, DMSO-d6) δ 9.92 (s, 1 H, OH), 8.34 (s, 1 H, H6), 7.77 (d, J=9.0 Hz, 1 H, H4), 7.19 (dd, J=9.0, 2.6 Hz, 1 H, H3), 7.12 (d, J=2.6 Hz, 1 H, H1), 2.88 (t, J=6.1 Hz, 2 H, H7 or H10), 2.78 (t, J=6.1 H, 2 H, H7 or H10), 1.87-1.74 (m, 4 H, H8 and H9); 13C NMR (125 MHz, DMSO -d6) δ 155.5, 148.8, 141.1, 138.5, 130.9, 129.4, 128.4, 120.0, 104.0, 26.5, 24.3, 22.1, 21.9; MS (FAB+) m/e (rel intensity) 200 (M+H, 100), 124 (8), 107 (14); HRMS for C13H14NO (M+H), calcd 200.1075, found 200.1079.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-aaad9653b81a46e5b4c25b09ccc32f34
Source dataset
uspto-grants-1994_01
Patent number
US05281710

Reaction notes

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