Methanol → 6-Chloropyridine-3-carbaldehyde

HRID 2424420Notes

Reaction equation

HRID 2424420 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#N)=[CH:4][N:3]=1.CC(C[AlH]CC(C)C)C.CO.[OH:21]S(O)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]=[O:21])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 27640536-Chloropyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

2-Chloro-5-cyanopyridine (5 g, 36 mmol) was dissolved in anhydrous toluene (100 ml) and cooled to 5° C. 1.5M DIBAL-H in toluene (25.2 ml, 38 mmol) was added dropwise over 20 min. The resulting solution was treated with MeOH (10 ml) and then 2M H2SO4 (30 ml) and stirred at room temp. for 48 h. The mixture was concentrated and the residue partitioned between EtOAc and water. The organic layer was separated, washed with brine and saturated NaHCO3 solution, then dried (Na2SO4) and concentrated to give the title compound as a pale yellow solid (5.419). δH (CDCl3) 7.51 (1H, d), 8.14 (1H, m), 8.87 (1H, d), 10.10 (1H, s).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with brine and saturated NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94168415f7724561977a5b4bb8898821
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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