2-Amino-5,7-diethyl-3-phenyl-1,6-naphthyridine → 5,7-diethyl-3-phenyl-1,6-naphthyridin-2(1H)-one

HRID 487397Notes

Reaction equation

HRID 487397 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH2:24][CH3:25])=[N:11][C:12]=2[CH2:22][CH3:23])[N:7]=1>O.Cl>[CH2:22]([C:12]1[N:11]=[C:10]([CH2:24][CH3:25])[CH:9]=[C:8]2[C:13]=1[CH:14]=[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6](=[O:2])[NH:7]2)[CH3:23]

Participants

5

Reactant 2

HCID 190936722-Amino-5,7-diethyl-3-phenyl-1,6-naphthyridineHCID 23668193Sodium Nitrite

Product 1

HCID 190937045,7-diethyl-3-phenyl-1,6-naphthyridin-2(1H)-oneYield 49.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (3.2 g) in water (64 ml) was added dropwise over 45 minutes to a solution of compound B (2.0 g) in 2M hydrochloric acid (150 ml). The mixture was stirred for a further 1 hour and then the suspended white solid was collected by filtration and dried under vacuum to give 5,7-diethyl-3-phenyl-1,6-naphthyridin-2(1H)-one (1.0 g); m.p. >260° C.; NMR (d6 -DMSO): 1.32(t, 3H), 1.33(t, 3H), 3.07(q, 2H), 3.47(q, 2H), 7.41(s, 1H), 7.43-7.55(m, 3H), 7.74-7.85(m, 2H), 8.31(s, 1H); mass spectrum (+ve FAB, methanol/NBA): 279 (M+H)+ ; microanalysis, found: C, 76.9; H, 6.6; N, 9.7%; C18H18N2O.0.25H2O requires: C, 76.4; H, 6.5; N, 9.9 %.

Workup

  1. filtrationthe suspended white solid was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-66de91c8e59e461a8bc4924287942710
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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