Acetic Acid → n-Propyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenylquinolin-5-yl)-pyridine-3-carboxylate

HRID 1769259Notes

Reaction equation

HRID 1769259 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([CH:17]=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1O[N:23]=[CH:22][CH:21]=1.[Na].Cl.[C:27]([CH2:30][C:31]([O:33][CH2:34][CH2:35][CH3:36])=[O:32])(=[NH:29])[NH2:28].C(O)(=O)C>C(O)CC>[NH2:29][C:27]1[NH:28][C:20]([CH3:19])=[C:21]([C:22]#[N:23])[CH:17]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]3)[C:30]=1[C:31]([O:33][CH2:34][CH2:35][CH3:36])=[O:32]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 798335-MethylisoxazoleHCID 5360545SodiumHCID 12391079Propyl amidinoacetate hydrochlorideHCID 15170332HCID 15170332, compound

Product 1

HCID 67780612n-Propyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenylquinolin-5-yl)-pyridine-3-carboxylateYield 16.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

23.3 g (100 mmol) of 3-phenyl-quinoline-5-aldehyde are suspended in 200 ml of n-propanol and the suspension is stirred with 8.25 ml (100 mmol) of 5-methylisoxazole. A solution of 2.3 g of sodium in 100 ml of n-propanol is added dropwise and the mixture is stirred at 40°-50° C. for 4 hours. A brown solution is obtained by this procedure. 18.04 g (100 mmol) of propyl amidinoacetate hydrochloride and 6 ml of acetic acid (100 mmol) are added and the mixture is boiled for 20 hours. It is concentrated, the residue is dissolved in ethyl acetate/water and the phases are separated. The ethyl acetate phase is washed with sodium bicarbonate solution and twice with water, dried and concentrated. The resulting residue is dissolved in 100 ml of hot acetonitrile and the product is left to crystallise. It is filtered off with suction and recrystallised from n-propanol and then from acetonitrile. 6.9 g of colourless crystals of melting point 237° C. are obtained.

Workup

  1. customA brown solution is obtained by this procedure
  2. waitthe mixture is boiled for 20 hours
  3. concentrationIt is concentrated
  4. dissolutionthe residue is dissolved in ethyl acetate/water
  5. customthe phases are separated
  6. washThe ethyl acetate phase is washed with sodium bicarbonate solution and twice with water
  7. customdried
  8. concentrationconcentrated
  9. dissolutionThe resulting residue is dissolved in 100 ml of hot acetonitrile
  10. waitthe product is left
  11. customto crystallise
  12. filtrationIt is filtered off with suction
  13. customrecrystallised from n-propanol

Sources & evidence

ORD record
ord-3b6bdef469e2473ea9aa32ec1c78b1c6
Source dataset
uspto-grants-1995_01
Patent number
US05380851

Reaction notes

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