Hydrochloric Acid → HCID 86600156, compound

HRID 533950Notes

Reaction equation

HRID 533950 reaction equation
N([O-])=O.[Na+].CO[C:7]1[C:12](N)=[CH:11][CH:10]=[CH:9][N:8]=1.[CH:14]([CH:16]=[CH2:17])=[O:15].[O-2].[Ca+2].[ClH:20]>O.CC(C)=O>[Cl:20][CH:16]([CH2:17][C:12]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH:14]=[O:15]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7847AcroleinHCID 27374883-Amino-2-methoxypyridineHCID 6850728CalciumoxideHCID 23668193Sodium Nitrite

Product 1

HCID 86600156HCID 86600156, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (20. g, 0.28 mol) in water (100 mL) was slowly added to a solution of 2-methoxy-pyridin-3-ylamine (36 g, 0.25 mol) in hydrochloric acid (20% aqueous solution, 60 mL) at 0° C. After stirring for 10 minutes, a cooled (0° C.) solution of acrolein (25 mL, 0.37 mol) in acetone (25 mL) containing calcium oxide (5 g, 0.09 mol) was slowly added to the reaction mixture. This was then followed by a solution of cuprous chloride (2.5 g, 0.025 mol) in acetone (25 mL) containing hydrochloric acid (20% aqueous solution, 5 mL). The mixture was stirred at 0 to 30° C. for 3 hours, and then extracted three times with dichloromethane (150 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil. The crude product was passed through a short silica column to give a crude product, which was used directly in the next step.

Workup

  1. additionwas slowly added to the reaction mixture
  2. stirringThe mixture was stirred at 0 to 30° C. for 3 hours
  3. extractionextracted three times with dichloromethane (150 mL)
  4. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give a black viscous oil

Sources & evidence

ORD record
ord-0fbe086263b2426c9c5b4dac197ff16c
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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