Hydrochloric Acid → HCID 88656388, compound

HRID 542889Notes

Reaction equation

HRID 542889 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.C[O:11][CH:12](OC)[CH2:13][CH:14](OC)OC.C(=O)(O)[O-].[Na+]>C(O)C.O>[CH:12]([CH:13]=[CH:14][NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 153472-Amino-3-methylpyridineHCID 66019TetramethoxypropaneHCID 516892Sodium Bicarbonate

Product 1

HCID 88656388HCID 88656388, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-amino-3-methylpyridine (53.9 g) and anhydrous hydrogen chloride (40 g) in anhydrous ethanol (960 ml) was treated with 1,1,3,3-tetramethoxypropane and heated at reflux for 6 hours. The solution was then concentrated to dryness under reduced pressure and the residue was triturated with diethyl ether, to give crude 9-methylpyrido[1,2-a]pyrimidinium chloride (76 g). This crude salt was dissolved in water (300 ml) and treated with sodium bicarbonate (35.4 g). The mixture was stirred at room temperature for one hour and then it was filtered, washed with water and recrystallised from water, to give 1-formyl-2-(3-methylpyrid-2-ylamino)ethene (32.7 g), m.p. 129°-131° C. (with decomposition).

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. concentrationThe solution was then concentrated to dryness under reduced pressure
  4. customthe residue was triturated with diethyl ether
  5. customto give crude 9-methylpyrido[1,2-a]pyrimidinium chloride (76 g)
  6. filtrationit was filtered
  7. washwashed with water
  8. customrecrystallised from water

Sources & evidence

ORD record
ord-a37604ae97ba42cd8dd267c0471b5172
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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