Diethyl Ether → HCID 19093683, compound

HRID 487399Notes

Reaction equation

HRID 487399 reaction equation
[OH-:1].[K+].[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8](C(N)=O)[C:9](=[O:54])[N:10]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21](C2C=CC=CC=2C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=[CH:20][CH:19]=1)[CH3:4].C[CH2:59][O:60]CC>C(O)C>[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:59]([OH:60])=[O:1])=[CH:22][CH:23]=1)[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 19093751HCID 19093751, compound

Product 1

HCID 19093683HCID 19093683, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (0.112 g) was added to a solution of methyl 4-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)-methyl]benzoate (A) (0.35 g) in ethanol (10 ml) and the mixture was heated at reflux for 90 minutes. Volatile material was removed by evaporation and the residue was dissolved in a minimum of water which was then acidified with acetic acid. Ether was added to the mixture and the solid which crystallised was collected by filtration. Further solid was obtained by adding petroleum ether to the ether phase of the filtrate. The combined solids were recrystallised from ethyl acetate/petroleum ether to give 4-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoic acid (0.175 g), as a solid, m.p. 143°-146° C.; NMR (CDCl3): 1.21(t, 3H), 1.35(t, 3H), 2.79(q, 2H), 3.12(q, 2H), 5.56(s, 2H), 6.77(s, 1H), 6.80(d, 1H), 7.30(d, 2H), 7.81(d, 1H), 8.05(d, 2H); mass spectrum (CI. ammonia): 337 (M+H)+ ; microanalysis, found: C, 71.3; H, 6.3; N, 7.9%; C20H20N2O3 requires: C, 71.4; H, 6.0; N, 8.3%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. customVolatile material was removed by evaporation
  4. dissolutionthe residue was dissolved in a minimum of water which
  5. additionEther was added to the mixture
  6. customthe solid which crystallised
  7. filtrationwas collected by filtration
  8. customFurther solid was obtained
  9. customThe combined solids were recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-5e26232f619a4e978de0650d4dcd2902
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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