Water → HCID 66875540, compound

HRID 1162190Notes

Reaction equation

HRID 1162190 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:21])[C:18]=1[CH:19]=O.[BH4-].[Na+].O>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:21])[C:18]=1[CH2:19][NH:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 227703,4-DimethoxyanilineHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 66875540HCID 66875540, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available 3,4-dimethoxy-phenyl-amine (1.74 g, 11.3 mmoles) and 3,5-dichloro-pyridine-4-carbaldehyde (2.0 g, 11.3 mmoles) were dissolved in toluene (40 mL) under nitrogen atmosphere. Molecular sieves (4A, 1 g) were added, and the mixture was heated to reflux. Reaction monitoring was performed by TLC analysis (petroleum ether/AcOEt 7/3): formation of the imine intermediate was completed after 3 hours. Molecular sieves were removed by filtration and the solvent was evaporated. The residue was dissolved in ethanol (99%, 40 mL). The solution was cooled to 0° C. and NaBH4 (559 mg, 14.7 mmol) was added. The resulting mixture was stirred at room temperature for 18 hours, then water was added (50 mL), and the mixture was extracted AcOEt (3×60 mL). The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3). The title compound was obtained as a yellow solid (3.04 g).

Workup

  1. temperaturethe mixture was heated to reflux
  2. customReaction monitoring
  3. customMolecular sieves were removed by filtration
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in ethanol (99%, 40 mL)
  6. extractionthe mixture was extracted AcOEt (3×60 mL)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3)

Sources & evidence

ORD record
ord-dd33cc04dd624c47a0198fe63ce6ac0d
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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