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

HRID 1052075

反応式

HRID 1052075 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-945b06cc57b341dca03333029dc586cd
出典データセット
uspto-grants-2016_07
特許番号
US09388176B2

関連ノート

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