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

HRID 2173381Notes

Reaction equation

HRID 2173381 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-01e4cf7dc6e242ffb41f088fee507bbf
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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