Hydrochloric Acid → 3-(1,2-dicarboxyethyl)-3-(3-oxobutyl)-imidazo[1,2-a]pyridin-2(3H)-one

HRID 1981338Notes

Reaction equation

HRID 1981338 reaction equation
Cl.[C:2]([CH:5]([CH:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]1=[O:19])[CH2:6][C:7]([OH:9])=[O:8])([OH:4])=[O:3].[CH:20]([C:22]([CH3:24])=[O:23])=[CH2:21].CO>O>[C:2]([CH:5]([C:10]1([CH2:21][CH2:20][C:22](=[O:23])[CH3:24])[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]1=[O:19])[CH2:6][C:7]([OH:9])=[O:8])([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6570Methyl vinyl ketoneHCID 203995172-(2-Oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)butanedioic acid

Product 1

HCID 203995153-(1,2-dicarboxyethyl)-3-(3-oxobutyl)-imidazo[1,2-a]pyridin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.9 g (0.066 mole) of the hydrochloride of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one, 7 g (0.1 mole) of methyl vinyl ketone, 50 ml of methanol and 50 ml of water is stirred at room temperature for 36 hours. The product is then precipitated by the dropwise addition of approximately 15 ml of 4N aqueous sodium hydroxide solution. The precipitate is filtered with suction, washed with water, methanol and acetone and dried in vacuo at 50° C. 8 g (38% of the theoretical yield) of 3-(1,2-dicarboxyethyl)-3-(3-oxobutyl)-imidazo[1,2-a]pyridin-2(3H)-one having a melting point of 195° C. (decomposition) are obtained.

Workup

  1. customThe product is then precipitated by the dropwise addition of approximately 15 ml of 4N aqueous sodium hydroxide solution
  2. filtrationThe precipitate is filtered with suction
  3. washwashed with water, methanol and acetone
  4. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-3d1ea877d32141ec9a008ad2e6cc2424
Source dataset
uspto-grants-1985_04
Patent number
US04514415

Reaction notes

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