Hydrochloric Acid → Methyl 6-(hydroxymethyl)picolinate

HRID 1889721Notes

Reaction equation

HRID 1889721 reaction equation
C[C:2]1([C:13]([O-])=[O:14])[NH:7][C:6]([C:8]([O:10][CH2:11]C)=[O:9])=[CH:5][CH:4]=[CH:3]1.[BH4-].[Na+].Cl>CO.C(Cl)Cl>[OH:14][CH2:13][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86659765HCID 86659765, compound

Product 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinateYield 108.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-ethyl 6-methylpyridine-2,6-dicarboxylate (3.0 g, 14.3 mmol) in MeOH (20 mL) and CH2Cl2 (10 mL) was added slowly NaBH4 (1.95 g, 51.6 mmol) in several portions at −40° C. After 10 min, the reaction mixture was stirred at rt for 1 h. To the reaction mixture was added 5 mL of 1 N HCl and the mixture was stirred for 20 min. The solvents were removed in vacuo and the residue was diluted with CHCl3 and saturated aqueous NaHCO3 solution (20 mL). The organic layer was separated, dried over MgSO4, filtered and the filtrate solution was concentrated in vacuo to give the desired compound (2.6 g, 54%) as a white solid. 1H NMR (DMSO-d6) δ 8.02 (t, J=8.0 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 4.62 (d, J=8.0 Hz, 2H), 3.88 (s, 3H). MS (ESI): 168.1 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 20 min
  2. customThe solvents were removed in vacuo
  3. additionthe residue was diluted with CHCl3 and saturated aqueous NaHCO3 solution (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2e58a0c1541c4ba49b4287b0f648219a
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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