Ethanol → 7-Methoxy-1H-indole-3-carboxylic acid

HRID 1089532ノート

反応式

HRID 1089532 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH2:13]([OH:15])C>[OH-].[Na+]>[CH3:13][O:15][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[C:3]2[C:10]([OH:12])=[O:11]

参加物

4

反応物 2

HCID 702EthanolHCID 69867Indole-3-Carboxylic Acid

生成物 1

HCID 150679677-Methoxy-1H-indole-3-carboxylic acid収率 47%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

Preparation of 5 was based on a procedure for the synthesis of indole-3-carboxylic acid reported by R. K. Mackie et al. [supra]. To a 200-mL round bottom flask, 2.369 g of 4 (9.75 mmol) was added. Compound 4 was dissolved in 19 mL of absolute ethanol and 53 mL of 5N aqueous sodium hydroxide, refluxed overnight, and allowed to cool. The ethanol was removed by rotary evaporation, and the resulting solution was extracted with two 25-mL portions of diethyl ether. The aqueous solution was acidified with concentrated hydrochloric acid, and the peach-colored precipitate was collected. Recrystallization from hot aqueous ethanol (50:50 ethanol:water) yielded 0.883 g (47%) of 5 as cream-colored crystals: 1H NMR (acetone-d6) δ 3.95 (s, 3H, OCH3), 6.76 (d, 1H, J=7.3 Hz), 7.10 (app. t, 1H, J=8 Hz), 7.71 (d, 1H, J=8.5 Hz), 7.95 (m, 1H), 11.0 (br s, 1H).

後処理

  1. customPreparation of 5
  2. temperatureto cool
  3. customThe ethanol was removed by rotary evaporation
  4. extractionthe resulting solution was extracted with two 25-mL portions of diethyl ether
  5. customthe peach-colored precipitate was collected
  6. customRecrystallization from hot aqueous ethanol (50:50 ethanol:water)

出典と根拠

ORDレコード
ord-d73dcd1092c549afa1619207c67d11a7
出典データセット
uspto-grants-1990_10
特許番号
US04966913

反応ノート

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