Triethylamine → diethyl 3-(m-chlorophenyl)-4-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6,7-dicarboxylate

HRID 864904Notes

Reaction equation

HRID 864904 reaction equation
[C:1]([C:4]1[C:9](=O)[NH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=1)(=O)[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[CH:26][CH:27]=1.C(N(CC)CC)C.[OH-].[NH4+]>C(OC(=O)C)(=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([C:28]2[C:29](=[O:31])[O:30][C:9]3=[N:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[C:4]3[C:1]=2[CH3:2])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 158793-Chlorophenylacetic acidHCID 13752508Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 19958197diethyl 3-(m-chlorophenyl)-4-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6,7-dicarboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Diethyl 5-acetyl-1, 6-dihydro-6-oxo-2,3-pyridinedicarboxylate (12.0 g, 0.043 mol), 3-chlorophenyl acetic acid (7.33 g, 0.043 mol) and triethylamine (6.52 g) are refluxed in 120 mL of acetic anhydride for three hours. The reaction mixture is cooled, poured into 120 mL of ice-cold water and made alkaline to pH 8 with an ammonium hydroxide solution. The crystalline solid is filtered and washed with water to give (17.0 g, 95%) of the product after drying. Recrystallization from ethyl acetate affords the pure product (13.29, 74% yield), melting point 170°-172° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe crystalline solid is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-0817ae00764243d3aa6b66c6974e83a1
Source dataset
uspto-grants-1996_10
Patent number
US05565411

Reaction notes

Loading…