Acetic Acid → 3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoic acid

HRID 338763

Reaktionsgleichung

Reaktionsgleichung von HRID 338763
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16]CC)=[O:15].[OH-].[Na+].C(O)(=O)C>O1CCOCC1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([OH:16])=[O:15]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86695877Ethyl 3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoate

Produkt 1

HCID 866958783-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of ethyl 3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoate (51 mg, 0.18 mmol) and 0.5 mL 1.0 M NaOH in 2.0 mL dioxane was heated at 70° C. for 2.3 hours. The pH of the reaction was adjusted to pH 5 using glacial acetic acid. The mixture was evaporated and then chased with MeOH to give a yellow solid film. An impure lot from a previous reaction was combined, and this material triturated with EtOAc. The remaining solid was dissolved in MeOH, and then Bio-rad AG1-X8 basic resin (hydroxide form) was added. The mixture was filtered and the resin rinsed with MeOH and CH2Cl2. The product was eluted from the resin using 10% formic acid in MeOH. The solvent was evaporated, chased with MeOH and EtOAc to give the title compound (used as is for the next step) as a yellow solid (49 mg). 1H NMR (CD3OD) δ: 8.42 (s, 1H), 8.29 (d, J=5.3 Hz, 1H), 7.68-7.70 (m, 1H), 7.48-7.51 (m, 1H), 7.33-7.39 (m, 1H), 7.30 (dd, J=2.5, 1.3 Hz, 1H), 7.26 (d, J=4.7 Hz, 1H), 4.48 (s, 2H), 3.64 (t, J=5.9 Hz, 2H), 3.04 (t, J=5.6 Hz, 2H).

Aufarbeitung

  1. customThe mixture was evaporated
  2. customto give a yellow solid film
  3. customAn impure lot from a previous reaction
  4. customthis material triturated with EtOAc
  5. dissolutionThe remaining solid was dissolved in MeOH
  6. additionBio-rad AG1-X8 basic resin (hydroxide form) was added
  7. filtrationThe mixture was filtered
  8. washthe resin rinsed with MeOH and CH2Cl2
  9. washThe product was eluted from the resin
  10. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-247b5f0dbab843a0802831846b268282
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889870B2

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