Diethylene Glycol → 2-(6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridin-3-yl)acetic acid

HRID 1928534Notes

Reaction equation

HRID 1928534 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]([C:18](=O)[C:19]([OH:21])=[O:20])[CH:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(O)COCCO.O.NN.[OH-].[K+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]([OH:21])=[O:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 68620027HCID 68620027, compound

Product 1

HCID 114259872-(6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridin-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

In a clean round bottom flask was charged oxoacetic acid (68 mmol) from example 1, 100 ml of diethylene glycol, hydrazine hydrate (184 mmol) and potassium hydroxide (115 mmol). The reaction mixture was heated to a temperature of 120-180° C. The reaction was monitored by TLC. After completion of the reaction, the reaction mass was cooled to room temperature and 100 ml of water was added. The reaction mass was further cooled to 0-10° C. and the pH was adjusted to 6-6.5 using acetic acid and stirred for 1 hour. The solid obtained was filtered, washed with water and dried in oven at 90-100° C. Yield: 16 gm of the title compound, m.p. 228-230° C. Purity 97% (HPLC).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mass was cooled to room temperature
  3. temperatureThe reaction mass was further cooled to 0-10° C.
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in oven at 90-100° C

Sources & evidence

ORD record
ord-cac5e8c5a76549ecb93f7607321569e8
Source dataset
uspto-grants-2012_05
Patent number
US08183377B2

Reaction notes

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