Hydrochloric Acid → Methyl 2-amino-6-(hydroxymethyl)pyridine-3-carboxylate

HRID 570721Notes

Reaction equation

HRID 570721 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(O)C>[NH2:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86685382Dimethyl 6-aminopyridine-2,5-dicarboxylate

Product 1

HCID 86685381Methyl 2-amino-6-(hydroxymethyl)pyridine-3-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Dimethyl 6-aminopyridine-2,5-dicarboxylate (395 mg) was suspended in a mixed solvent (16 ml) of tetrahydrofuran/ethanol (1/1), calcium chloride (834 mg) and sodium borohydride (85.5 mg) were added thereto under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was acidified with 1M hydrochloric acid, basified with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (296 mg) as a white solid.

Workup

  1. additionwere added
  2. temperatureunder ice-cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4d5ea7273da44bb8b528f4288e0225f
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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