Trifluoroacetic acid → 2-Oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylic acid

HRID 347541노트

반응식

HRID 347541 반응식
[O:1]=[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[Na+].C(O)(C(F)(F)F)=O>CO>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 21081726Methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylate

생성물 1

HCID 210815862-Oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylic acid수율 55.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylate (500 mg, 2.17 mmol) and 3 N NaOH (1 mL) and methanol (10 mL) was stirred at rt overnight. To the reaction was added TFA (0.5 mL) and the mixture was concentrated in vacuo. The residue was dissolved in water (3 mL) and i-PrOH (10 mL). The solid which formed was filtered, washed with a small amount of water and i-PrOH, and dried to obtain the acid (260 mg, 55%) as a white solid. 1H NMR (DMF-d7) δ 14.14 (br s, 1H), 8.72 (d, 1H, J=4.9 Hz), 8.62 (dd, 1H, J=7.7, 2.2 Hz), 8.47 (dd, 1H, J=6.6, 2.2 Hz), 8.18–7.98 (m, 2H), 7.67 (dd, 1H, J=7.2, 5.3 Hz), 6.97 (t, 1H, J=6.6 Hz); MS(ESI+) m/z 217.2 (M+H)+.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water (3 mL)
  3. customThe solid which formed
  4. filtrationwas filtered
  5. washwashed with a small amount of water and i-PrOH
  6. customdried

출처 및 근거

ORD 기록
ord-448b9c9d74ca4854962652a010be403d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

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