Acetoacetic Acid → 2,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid

HRID 847786Notes

Reaction equation

HRID 847786 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH2:8]1N2CN3CN(C2)CN1C3.[C:18]([O-:21])(=[O:20])[CH3:19].[NH4+:22].[CH2:23](O)[CH3:24]>>[CH3:5][C:3]1[NH:22][C:23]([CH3:24])=[C:19]([C:18]([OH:21])=[O:20])[CH2:8][C:2]=1[C:1]([OH:7])=[O:6]

Participants

5

Reactant 4

HCID 96Acetoacetic AcidHCID 702EthanolHCID 4101HexamethylenetetramineHCID 517165Ammonium Acetate

Product 1

HCID 157329562,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid

Procedure

A mixture of 22.2 g of bornyl ester of acetoacetic acid 7 g of hexamethylenetetramine, 3.9 g of ammonium acetate and 150 ml of ethyl alcohol is refluxed for 30 minutes. After cooling a yellow substance is precipitated which is then filtered-off and recrystallized from ethanol. There are obtained 12 g (52% of the theoretical value) of bornyl ester of 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid as a yellow crystalline substance having melting point of 171°-173° C.

Workup

  1. temperatureis refluxed for 30 minutes
  2. temperatureAfter cooling a yellow substance
  3. customis precipitated which
  4. customfiltered-off and recrystallized from ethanol

Sources & evidence

ORD record
ord-7b4222457ed74e08a8552fc5b0b5a9ac
Source dataset
uspto-grants-1981_10
Patent number
US04293700

Reaction notes

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