Methyl 7-nitrobenzofuran-4-carboxylate → Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364661ノート

反応式

HRID 2364661 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]2[C:12]=1[O:11][CH:10]=[CH:9]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]2[C:12]=1[O:11][CH2:10][CH2:9]2

参加物

4

反応物 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate

生成物 1

HCID 68107686Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate収率 62.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒2 回

実験手順

Methyl 7-nitrobenzofuran-4-carboxylate 1f (820 mg, 3.70 mmol) was dissolved in 150 mL of methanol in an ice-water bath, added with (164 mg, 10%) palladium/carbon, methanol (0.3 mL). The resulting solution was subjected to hydrogenation for 16 hours at 3 atmosphere at room temperature. The resulting mixture was filtered and washed with 50 mL of methanol, concentrated under reduced pressure. The crude residue was recrystallised by the mixture solvent of 25 mL ethyl acetate and n-hexane (V/V=1:4) to obtain the title compound methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate 1g (446 mg, yield: 62.0%) as a gray solid.

後処理

  1. filtrationThe resulting mixture was filtered
  2. washwashed with 50 mL of methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was recrystallised by the mixture solvent of 25 mL ethyl acetate and n-hexane (V/V=1:4)

出典と根拠

ORDレコード
ord-2d982ef75d1a4446a41cb0a5153faed8
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

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