Citric Acid → 6-(2-Cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570330
[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 71280906Ethyl 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 712807766-(2-Cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirring mixture of ethyl 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylate (74) (100 mg, 0.411 mmol) and 2N LiOH (0.2 mL) in THF:MeOH (4:1, 3 mL) was heated at 50° C. for 45 minutes. The reaction was cooled to room temperature and the pH was adjusted between 3-5 with 10% citric acid. The solvent was partially reduced. The resulting solid was collected by vacuum filtration and washed with excess water. Crude 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (75) was dried and used in the next step without further purification. MS m/z 416.07 (M+1)+.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with excess water
  4. dry with materialCrude 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (75) was dried
  5. customused in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b4be23751ed14cf1b13485210300005c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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