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Basic Information
CAS No.: 189005-44-5
Name: 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid
Article Data: 21
Molecular Structure:
Molecular Structure of 189005-44-5 (6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid)
Formula: C17H16N2O2
Molecular Weight: 280.326
Synonyms: Zolpidicacid;2-(4-Methylphenyl)-6-methylimidazole[1,2-a]-pyridine-3-acetic Acid;imidazo[1,2-a]pyridine-3-acetic acid, 6-methyl-2-(4-methylphenyl)-;[6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid;
EINECS: 606-162-4
Density: 1.224 g/cm3
Melting Point: 243-245 °C
Appearance: Off-white to pale beige solid
PSA: 54.60000
LogP: 3.24520
Synthetic route
193979-47-4

ethyl 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetate

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With water; potassium hydroxide In ethanol at 30℃;96%
With sodium hydroxide In water for 3h; Reflux;81.8%
With water; sodium hydroxide In ethanol at 90℃; Flow reactor;
82626-48-0

N,N,6-trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 0℃; for 18h; Heating / reflux;94%
79-37-8

oxalyl dichloride

88965-00-8

6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
Stage #1: oxalyl dichloride; 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine With potassium carbonate In tetrahydrofuran at 20 - 35℃;
Stage #2: With potassium hydroxide In tetrahydrofuran; water at 65 - 70℃;
Stage #3: With hydrazine hydrate In water at 110 - 115℃; Reagent/catalyst; Temperature; Solvent;
95.2%
1603-41-4

(5-methyl-pyridin-2-yl)amine

53515-23-4

3-bromo-4-(4-methylphenyl)-4-oxobutanoic acid

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With sodium carbonate In water at 60℃; for 6h; Concentration; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;82%
1603-41-4

(5-methyl-pyridin-2-yl)amine

68261-97-2

3-chloro-4-(4-methylphenyl)-4-oxobutanoic acid

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With sodium carbonate In water at 80℃; for 7h; Concentration; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;52%
768398-03-4

6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With hydrogenchloride; water91%
Stage #1: 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine With sulfuric acid; water at 110℃; for 4 - 5h;
Stage #2: With sodium hydroxide; water at 0℃; pH=9;
Stage #3: With water; acetic acid pH=5.5; Product distribution / selectivity;
72%
Stage #1: 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine With hydrogenchloride In water at 25 - 100℃; for 12h; Heating / reflux;
Stage #2: With potassium hydroxide In water at 25 - 105℃; for 2 - 3h;
Stage #3: With acetic acid In water at 30 - 40℃;
Stage #1: 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine With sodium hydroxide; water at 55 - 98℃; for 16.5h; Heating / reflux;
Stage #2: With acetic acid In water at 25℃; for 4h; pH=5.3;
With sulfuric acid at 110℃; Inert atmosphere;
927820-48-2

(6-methyl-2-p-tolyl-2,3-dihydro-imidazo[1,2-a]pyridin-3-yl)-oxoacetic acid

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
Stage #1: (6-methyl-2-p-tolyl-2,3-dihydro-imidazo[1,2-a]pyridin-3-yl)-oxoacetic acid With potassium hydroxide; hydrazine In diethylene glycol at 120 - 180℃; pH=4 - 5;
Stage #2: With acetic acid In water; diethylene glycol at 0 - 10℃; pH=6 - 6.5;

potassium 2-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetate

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With acetic acid In water; acetone at 0 - 10℃; for 0.5h;67%
88965-00-8

6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 78 percent / acetic acid / H2O / 4 h / 50 - 55 °C
2.1: MeI / ethanol / 24 h / 20 °C
2.2: H2O; ethanol / 4 h / Heating
3.1: 87 percent / aq. KOH / ethanol / 8 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 79 percent / AcOH
4: 91 percent / H2O, HCl
View Scheme
Multi-step reaction with 2 steps
1: ferrocene; bis(1-methyl-1-phenylethyl)peroxide / 20 h / 20 - 100 °C / Inert atmosphere; Sealed tube
2: sulfuric acid / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: tris(bipyridine)ruthenium(II) dichloride hexahydrate / methanol; water / 36 h / 20 °C / Irradiation; Inert atmosphere
2: potassium hydroxide / water; ethanol / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: rhodium (II) octanoate dimer / chloroform / 4 h / 20 °C / Inert atmosphere
2: lithium hydroxide monohydrate / methanol; water / 1 h / 20 °C
View Scheme
365213-58-7

2-(4-methylphenyl)-6-methylimidazo[1,2-α]pyridine-3-acetamide

189005-44-5

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 8h; Heating;87%
Downstream Products
258273-50-6
82626-48-0
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Chemistry

Molecular Structure of 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid (CAS NO.189005-44-5): 

Empirical Formula: C17H16N2O2
Molecular Weight: 280.3211
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 3
Polar Surface Area: 54.6 Å2
Index of Refraction: 1.631
Molar Refractivity: 81.588 cm3
Molar Volume: 229.068 cm3
Surface Tension: 45.987 dyne/cm
Density: 1.224 g/cm3
CAS: 189005-44-5
SMILES: O=C(O)Cc1c(nc2ccc(cn12)C)c3ccc(cc3)C
InChI: InChI=1/C17H16N2O2/c1-11-3-6-13(7-4-11)17-14(9-16(20)21)19-10-12(2)5-8-15(19)18-17/h3-8,10H,9H2,1-2H3,(H,20,21)
Product Categories: Heterocyclic Compounds; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

Specification

  6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid, with CAS number of 189005-44-5, can be called [6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid ; imidazo[1,2-a]pyridine-3-acetic acid, 6-methyl-2-(4-methylphenyl)- ; 2-(4-Methylphenyl)-6-methylimidazole[1,2-a]-pyridine-3-acetic Acid . It is an off-white to pale beige solid. 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid (CAS NO.189005-44-5) can be as an intermediate in the synthesis of Zolpidem.