Methanol → HCID 19093773, compound

HRID 487406Notes

Reaction equation

HRID 487406 reaction equation
[OH-:1].[Na+].[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[C:7](SC1C=CC=CC=1)=[CH:8][C:9](=[O:54])[N:10]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=[CH:20][CH:19]=1)[CH3:4].[CH3:62][OH:63]>>[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:54])[N:10]2[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:29]([C:62]([OH:63])=[O:1])=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:22][CH:23]=1)[CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19093748HCID 19093748, compound

Product 1

HCID 19093773HCID 19093773, compound

Procedure

2M Sodium hydroxide solution (3 ml) was added to a solution of methyl 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-carboxylate (A) (300 mg) in methanol (5 ml) and the mixture was heated at reflux for 2 hours. The mixture was cooled to ambient temperature and volatile material was removed by evaporation. The residue was dissolved in water and the solution adjusted to pH 5 with acetic acid. The precipitated solid was collected by filtration to give 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-carboxylic acid (100 mg) as a solid; m.p. 238°-240° C.; NMR (d6 -DMSO): 1.18(t, 3H), 1.26(t, 3H), 2.72(q, 2H), 3.60(q, 2H), 5.2(s, 2H), 6.70(d, 1H), 7.15(s, 1H), 7.23-7.71(m, 5H), 8.21(d, 1H), 12.65(broad s, 1H); mass spectrum (+ve FAB, methanol/NBA): 435 (M+Na)+, 413(M+H)+ ; microanalysis, found: C, 74.1; H, 5.6; N, 6.5%; C26H26N2O3.0.5.H2O requires; C, 74.0; H, 5.9; N, 6.6%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customvolatile material was removed by evaporation
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-3b4b6dcda17149fc9439cd07f82f3513
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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