Benzyl Chloride → 3-benzyloxy-4-benzyloxycarbonyl-1-methyl-2(1H)-pyridinone

HRID 54891Notes

Reaction equation

HRID 54891 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6](=[O:11])[C:5]=1[OH:12])([OH:3])=[O:2].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([O:12][C:5]1[C:6](=[O:11])[N:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[C:1]([O:3][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 546960643-Hydroxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 104504733-benzyloxy-4-benzyloxycarbonyl-1-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Carboxy-1-methyl-3-hydroxy-2(1H)-pyridinone (6.8 g, 0.04 mol) is mixed with benzyl chloride (12.1 g, 0.088 mol), anhydrous potassium carbonate (13.8 g, 0.1 mol) in anhydrous dimethyl-formamide (DMF) (120 mL). The mixture is heated at 75°-80° C. under N2 in darkness for 16 hours. The reaction mixture is filtered and rotary evaporated to yield a dark oil, which is purified by a silica gel plug as mentioned in 1-methyl-3-hydroxy-2(1H)-pyridinone to give the 3-benzyloxy-4-benzyloxycarbonyl-1-methyl-2(1H)-pyridinone as a pale yellow, thick oil. It is mixed with methanol (50 mL) and a 6M NaOH solution (10 mL). The mixture is stirred at room temperature for 4 hours, then evaporated to dryness. The residue is dissolved in water (100 mL), and acidified with 6M HCl solution to pH 2 to give the title compound (9.3 g 88.7%), as a white crystalline product, m.p. 152°-153° C. 1H NMR(250 MHz, CDCl3): δ3.616 (s, 3H),5.611 (s, 2H), 6.695 (d, 1H, J=7.13),7.152 (d, 1H, J=7.16), 7.35-7.48 (m, 5H). Anal. for C14H13NO4. 0.2H2O (262.87), Calcd. (found): C, 63.97 (64.05); H, 5.14 (5.14); N, 5.33 (5.18).

Workup

  1. temperatureThe mixture is heated at 75°-80° C. under N2 in darkness for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. customrotary evaporated
  4. customto yield a dark oil, which
  5. customis purified by a silica gel plug

Sources & evidence

ORD record
ord-6426c2278c2f4394b14dd25fdff704cc
Source dataset
uspto-grants-1997_04
Patent number
US05624901

Reaction notes

Loading…