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

HRID 1502141Notes

Reaction equation

HRID 1502141 reaction equation
C1(C(=[N:14][C:15]2[N:20]=[C:19]([CH2:21][C:22]([O-:24])=[O:23])[CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[CH2:26]1COCC1.O>>[NH2:14][C:15]1[N:20]=[C:19]([CH2:21][C:22]([O:24][CH3:26])=[O:23])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21881883Oxolane--water (1/1)HCID 131734294{6-[(Diphenylmethylidene)amino]pyridin-2-yl}acetate

Product 1

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

Procedure

{6-[(diphenylmethylidene)amino]pyridin-2-yl}acetate (1.3 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.

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-9b1c6dba44aa414ea260f64024ea803d
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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