Hydrochloric Acid → HCID 57464352, compound

HRID 533954Notes

Reaction equation

HRID 533954 reaction equation
[O:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1N)[CH3:2].N([O-])=O.[Na+].[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:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[O:1][CH3:2])[CH:14]=[O:15]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 70002-MethoxyanilineHCID 7847AcroleinHCID 6850728CalciumoxideHCID 23668193Sodium Nitrite

Product 1

HCID 57464352HCID 57464352, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-methoxylaniline (24.6 g, 0.200 mol) in hydrochloric acid (20% aqueous solution, 80 mL) was slowly added to a solution of sodium nitrite (15 g, 0.22 mol) in water (40 mL) at 0 to 5° C. After stirring for 10 minutes, a cooled (0° C.) solution of acrolein (30 g, 0.56 mol) in acetone (200 mL) containing calcium oxide (4.0 g, 72 mmol) was slowly added, followed by a solution of cuprous chloride (2.0 g, 20 mmol) in acetone (20 mL) containing hydrochloric acid (20% aqueous solution, 4 mL). The mixture was stirred at 0 to 30° C. for 3 hours, and then extracted with three 150 mL portions of dichloromethane. 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 concentrated to give a black viscous oil. The crude product was passed through a short silica column to give 10 g of crude product, which was used directly in the next procedure.

Workup

  1. additionwas slowly added
  2. stirringThe mixture was stirred at 0 to 30° C. for 3 hours
  3. extractionextracted with three 150 mL portions of dichloromethane
  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. concentrationconcentrated
  8. customto give a black viscous oil

Sources & evidence

ORD record
ord-2630fc6e3cbd472c9e6ae296a5d944fb
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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