Hydrochloric Acid → [Allyl-(5,6-dichloro-pyridin-3-yl)-amino]-acetaldehyde

HRID 899339Notes

Reaction equation

HRID 899339 reaction equation
[CH2:1]([N:4]([C:11]1[CH:12]=[N:13][C:14]([Cl:18])=[C:15]([Cl:17])[CH:16]=1)[CH2:5][CH:6](OC)[O:7]C)[CH:2]=[CH2:3].Cl.ClCCl>O1CCCC1.O>[CH2:1]([N:4]([CH2:5][CH:6]=[O:7])[C:11]1[CH:12]=[N:13][C:14]([Cl:18])=[C:15]([Cl:17])[CH:16]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 57448418Allyl-(5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)amine

Product 1

HCID 57448419[Allyl-(5,6-dichloro-pyridin-3-yl)-amino]-acetaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

A solution of allyl-(5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)-amine (57.2 g) in tetrahydrofuran (443 g) was cooled to 10° C. A solution of concentrated hydrochloric acid (136 g) in water (114 g) was slowly added, maintaining the temperature below 20° C. The reaction was then stirred at 15° C. for about 4 hours. Then dichloromethane (570 g) and water (430 g) were added and the layers separated. The organic layer was washed with 5% aqueous sodium bicarbonate (453 g), and then washed twice with water (430 g). The organic layer was concentrated and the residue dissolved in dichloromethane (580 g).

Workup

  1. temperaturemaintaining the temperature below 20° C
  2. customthe layers separated
  3. washThe organic layer was washed with 5% aqueous sodium bicarbonate (453 g)
  4. washwashed twice with water (430 g)
  5. concentrationThe organic layer was concentrated
  6. dissolutionthe residue dissolved in dichloromethane (580 g)

Sources & evidence

ORD record
ord-83ecfc65cbf348b2877a889aa4bd28e0
Source dataset
uspto-grants-2008_04
Patent number
US07354937B2

Reaction notes

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