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

HRID 443013Notes

Reaction equation

HRID 443013 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 dimethylformamide (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 the synthesis of 1-methyl-3-hydroxy-2(1H)pyridinone above, 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): δ 3.616 (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. 0.2 H2O (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
  6. customas mentioned in the synthesis of 1-methyl-3-hydroxy-2(1H)pyridinone above

Sources & evidence

ORD record
ord-6e2a99203e6c4c77b4cad41c5bde69ea
Source dataset
uspto-grants-1999_04
Patent number
US05892029

Reaction notes

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