Hydrochloric Acid → HCID 68598233, compound

HRID 573375Notes

Reaction equation

HRID 573375 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1(C(OCC)=O)[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][NH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl.[C:24](=O)(O)[O-:25].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([CH2:24][OH:25])[N:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68598245HCID 68598245, compound

Product 1

HCID 68598233HCID 68598233, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1.00 g (3.3 mmol) of ethyl 2-(t-butoxycarbonyl)amino-4-chloropicolinate and 20 mL of anhydrous ethanol, 0.38 g (10.0 mmol) of sodium borohydride was added, followed by stirring at room temperature for 17 hours. To the reaction solution, dilute hydrochloric acid was added thereby adjusting the pH to 2 and the solution was neutralized by adding saturated sodium bicarbonate aqueous solution. After ethanol was removed under reduced pressure, the resultant was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 (v/v)) to obtain 0.75 g (2.9 mmol, yield of 87%) of 2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine.

Workup

  1. additionwas added
  2. customAfter ethanol was removed under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 (v/v))

Sources & evidence

ORD record
ord-389243ea98694ab59774519d47e3afd8
Source dataset
uspto-grants-2015_05
Patent number
US09029552B2

Reaction notes

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