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

HRID 2117146ノート

反応式

HRID 2117146 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-3ef2e2ed928a4aab87fd4e2e15105d01
出典データセット
uspto-grants-2008_10
特許番号
US07439246B2

反応ノート

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