Hydrochloric Acid → 5-Bromo-6-(hydroxymethyl)nicotinaldehyde

HRID 1881731Notes

Reaction equation

HRID 1881731 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([Br:12])[C:7]([CH2:10][OH:11])=[N:8][CH:9]=1.Cl.[OH-].[Na+]>C(Cl)Cl>[Br:12][C:6]1[CH:5]=[C:4]([CH:3]=[O:2])[CH:9]=[N:8][C:7]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67428521{5-[Bis(methyloxy)methyl]-3-bromo-2-pyridinyl}methanol

Product 1

HCID 866648855-Bromo-6-(hydroxymethyl)nicotinaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of {5-[bis(methyloxy)methyl]-3-bromo-2-pyridinyl}methanol (98 mg, 0.374 mmol) and 1N HCl (3.26 mL, 3.26 mmol) in DCM (5 mL) was stirred overnight. DCM and 1M NaOH solution were added. Extraction, drying (Na2SO4), and filtration afforded 5-bromo-6-(hydroxymethyl)-3-pyridinecarbaldehyde (70 mg, 87%) as a brown oil pure enough to be used in the next step.

Workup

  1. extractionExtraction
  2. customdrying
  3. filtration(Na2SO4), and filtration

Sources & evidence

ORD record
ord-d4a25755496243068795a2cba435d0c2
Source dataset
uspto-grants-2012_11
Patent number
US08318940B2

Reaction notes

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