Potassium Hydroxide → 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 1821805ノート

反応式

HRID 1821805 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([O:13]CC)=[O:12])[NH:8][C:7]=12.[OH-].[K+]>O1CCCC1.CO>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[NH:8][C:7]=12

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 46839972ethyl 7-chloro-1H-pyrrolo(2,3-c)pyridine-2-carboxylate

生成物 1

HCID 768529167-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid収率 94.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.64 g, 2.85 mmol) was dissolved in tetrahydrofuran (5.7 mL) and methanol (6.8 mL). To the mixture was added 3 N KOH (2.85 mL). After stirring overnight (15.5 h) at room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in water. This aqueous solution was made acidic (pH 3) using 6 N HCl. The precipitate was collected by filtration. The precipitate was dissolved in methanol and concentrated to dryness to afford 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (0.53 g, 2.7=mmol, 94%) as a yellow powder: mp 210-214° C.; 1H NMR (300 MHz, CD3OD) δ7.25 (1H, s), 7.65 (1H, d, J=5.4 Hz), 7.94 (1H, d, J=5.4 Hz); ESI MS m/z 195 [C8H5ClN2O2—H]−; HPLC (Method A) >99% (AUC), tR=12.2 min.

後処理

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in water
  3. filtrationThe precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in methanol
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-d296640081d842e2a1fed356f4210d6b
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

反応ノート

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