Phenylacetonitrile → 2-Amino-5,7-diethyl-3-phenyl-1,6-naphthyridine

HRID 487396Notes

Reaction equation

HRID 487396 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=O.[OH-].[Na+].[C:16]1([CH2:22][C:23]#[N:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[NH2:24][C:23]1[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:3]2[C:2](=[CH:7][C:6]([CH2:8][CH3:9])=[N:5][C:4]=2[CH2:10][CH3:11])[N:1]=1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

Product 1

HCID 190936722-Amino-5,7-diethyl-3-phenyl-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-2,6-diethylpyridine-3-carbaldehyde (2.2 g), ethanol (26 ml), aqueous sodium hydroxide solution (10% w/v; 2.2 ml) and phenylacetonitrile (3.8 ml) was heated at reflux for 2 hours. Volatile material was removed by evaporation and the residue was partitioned between ethyl acetate and 2M hydrochloric acid. The organic phase was separated and discarded. The aqueous phase was adjusted to pH 6 with solid sodium carbonate and then extracted twice with dichloromethane. The combined extracts were dried (MgSO4) and solvent was removed by evaporation to give 2-amino-5,7-diethyl-3-phenyl-1,6-naphthyridine (B) as a pale yellow solid (3.2 g); m.p. 109.5°-112° C.; NMR (d6 -DMSO): 1.27(t, 3H), 1.28(t, 3H), 2.77(q, 2H), 3.09(q, 2H), 6.41(broad, 2H), 7.05(s, 1H), 7.4-7.6(m, 5H), 7.96(s, 1H); mass spectrum (+ve FAB, methanol/NBA): 278 (M+H)+ ; microanalysis, found: C, 68.1; H, 6.5; N, 13.1%; C18H19N3.HCl.0.25H2O requires: C, 68.0; H, 6.5; N, 13.2%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customVolatile material was removed by evaporation
  4. customthe residue was partitioned between ethyl acetate and 2M hydrochloric acid
  5. customThe organic phase was separated
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe combined extracts were dried (MgSO4) and solvent
  8. customwas removed by evaporation

Sources & evidence

ORD record
ord-337f9231022349869637722a5b6680c9
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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