Reaction #66928

Reaction equation

152

Dibenzyl 2-(1-naphthalenyl)-6,7-methylenedioxyquinolin-4-yl Phosphate

→

153

Yield 94.1%

2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-yl Dihydrogen Phosphate

Yield 94.1%

Solvents

MeOH

Conditions

Workup

1. 1
   OtherThe catalyst and precipitate were collected
2. 2
   workup.DISSOLUTIONdissolved in 10% NaHCO3 solution
3. 3
   Filtrationfiltered
4. 4
   Otherthe precipitate was then collected
5. 5
   Washwashed with acetone

Procedure

A suspension of 152 (894.8 mg, 1.55 mmol) in anhydrous MeOH (40 mL) was hydrogenated in the presence of 10% Pd/C (456.7 mg) at 25° C. for 15 min. The catalyst and precipitate were collected and dissolved in 10% NaHCO3 solution and then filtered. The filtrate was acidified with dil aq HCl and the precipitate was then collected and washed with acetone to give 153. Yellow solid; yield: 94.1%; ESI-MS (Negative mode): m/z 394 [M−H]−; 1H-NMR (D2O+NaOD, 500 MHz): δ 6.13 (2H, s), 7.26 (1H, s), 7.50 (1H, ddd, J=8.23, 7.33, 1.20 Hz), 7.55-7.58 (2H, m), 7.62-7.70 (3H, m), 7.98 (1H, d, J=8.53 Hz), 8.02 (1H, d, J=8.96 Hz); 13C-NMR (D2O+NaOD, 125 MHz): δ 98.65, 102.15, 103.54, 109.80, 110.00, 118.35, 125.66, 126.37, 126.84, 127.40, 128.34, 128.97, 130.89, 133.50, 138.15, 146.58, 147.34, 151.27, 158.15, 158.23.

Source