Hydrochloric Acid → Methyl 2-(6-aminopyridin-2-yl)acetate

HRID 2173381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173381
C1(C(=NC2N=C(CC(O)=O)C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:25][C:26]1[N:31]=[C:30]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:29]=[CH:28][CH:27]=1.Cl>C1COCC1.O>[NH2:25][C:26]1[N:31]=[C:30]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86693025Methyl (6-aminopyridin-2-yl)acetate {6-[(diphenylmethylidene)amino]pyridin-2-yl}acetate

Produkt 1

HCID 68841216Methyl 2-(6-aminopyridin-2-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

methyl (6-aminopyridin-2-yl)acetate {6-[(diphenylmethylidene)amino]pyridin-2-yl}acetate (13 g, 3.93 mmol) was dissolved in 1:1 mixture of THF/water (20 mL) and treated with 4.5 mL of a 1N aqueous hydrochloric acid solution. The reaction was allowed to stir at ambient temperature for 30 minutes and then concentrated in vacuo. The crude residue was dissolved in DCM and washed with a saturated aqueous sodium bicarbonate solution. The organic layers were dried over sodium sulfate, filtered and concentrated to afford crude methyl (6-aminopyridin-2-yl)acetate which, was used without further purification. LC/MS (M+H)+167. Step C: methyl [6-(1H-tetrazol-1-yl)pyridin-2-yl]acetate

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude residue was dissolved in DCM
  3. washwashed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-01e4cf7dc6e242ffb41f088fee507bbf
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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