Sodium Acetate → Isopropyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenyl-quinolin-5-yl)-pyridine-3-carboxylate

HRID 483606Notes

Reaction equation

HRID 483606 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.[NH2:19]/[C:20](/[CH3:24])=[CH:21]\[C:22]#[N:23].Cl.[C:26]([CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])(=N)[NH2:27].C([O-])(=O)C.[Na+]>C(O)(C)C>[NH2:27][C:26]1[NH:19][C:20]([CH3:24])=[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:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]3)[C:29]=1[C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 12391081Isopropyl amidinoacetate hydrochlorideHCID 151703323-Phenylquinoline-5-carbaldehyde

Product 1

HCID 9823672Isopropyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenyl-quinolin-5-yl)-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.66 g (20 mmol) of 3-phenyl-quinoline-5-aldehyde are boiled in 40 ml of isopropanol with 1.64 g (20 mmol) of 3-aminocrotononitrile, 3.6 g (20 mmol) of isopropyl amidinoacetate hydrochloride and 1.64 g (20 mmol) of sodium acetate for 20 hours. The mixture is concentrated, the residue is taken up in ethyl acetate/water and the phases are separated. The organic phase is washed twice with water, dried and concentrated. The reaction mixture is separated over a silica gel column using methylene chloride/ethyl acetate mixtures. The desired fractions are collected and concentrated. The resulting evaporation residue is crystallised with acetonitrile and filtered off with suction 635 mg of colourless crystals of melting point 227°-229° C. are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe phases are separated
  3. washThe organic phase is washed twice with water
  4. customdried
  5. concentrationconcentrated
  6. customThe reaction mixture is separated over a silica gel column
  7. customThe desired fractions are collected
  8. concentrationconcentrated
  9. customThe resulting evaporation residue
  10. customis crystallised with acetonitrile
  11. filtrationfiltered off with suction 635 mg of colourless crystals of melting point 227°-229° C.
  12. customare obtained

Sources & evidence

ORD record
ord-47e2a0a05461448797a1febcbc753667
Source dataset
uspto-grants-1993_07
Patent number
US05225558

Reaction notes

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