3,5-Dichloro-4-pyridinecarboxaldehyde → HCID 44190367, compound

HRID 1959567Notes

Reaction equation

HRID 1959567 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[CH:8]=[O:9].O.[SH-:12].[Na+].[BH4-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([SH:12])[C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 44190367HCID 44190367, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere a mixture of 3,5-dichloro-pyridine-4-carbaldehyde (3.00 g, 17.05 mmol) and sodium hydrosulfide hydrate (flakes 70%, 1.37 g, 17.05 mmol) in DMF (20 mL) was stirred at 0° C. for 15 min. NaBH4 (8.52 g, 17.05 mmol) was added. After 30 min at 0° C. the solution was filtered and the solvent was removed in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 176.0 [M+H+].

Workup

  1. filtrationAfter 30 min at 0° C. the solution was filtered
  2. customthe solvent was removed in vacuo
  3. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-3640facbbce447438df4cab28673de59
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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