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Ammonium formate → 4-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl ester

HRID 968478
ノート
印刷プレビュー

反応式

HRID 968478 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:19])[C:7]2[C:12]([CH:13]=1)=[C:11]([N+:14]([O-])=O)[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)=[O:4].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:19])[C:7]2[C:12]([CH:13]=1)=[C:11]([NH2:14])[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 206071685-Methoxy-1-methyl-4-nitroindole-2-carboxylic acid methyl ester

生成物 1

HCID 206071674-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl ester収率 67.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒2 回

実験手順

To a solution of 9 (1.0g, 3.78 mmol) in anhydrous methanol (90 mL) was added 10% Pd/C (150 mg) suspended in anhydrous methanol (15 mL) followed by ammonium formate (1.10 g, 17.4 mmol). The reaction mixture was stirred for 1 h, filtered through celite and the methanol removed. The residue was taken up in CH2Cl2/H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried over Na2SO4 and evaporated to afford 10 (595 mg, 67%) as a brown solid which was used without further purification; 1H NMR (CDCl3): δ 7.21 (1H, s), 7.06 (1H, d), 6.72 (1H, d), 4.01 (3H, s), 3.90 (3H, s), 3.88 (3H, s).

後処理

  1. filtrationfiltered through celite
  2. customthe methanol removed
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-dcfe474719944717ba8377a2f223018b
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07304046B2

反応ノート

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