Methanol → Methyl 1-(2-hydroxyethyl)-1H-benzimidazole-7-carboxylate

HRID 1991191ノート

反応式

HRID 1991191 の反応式
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:18]O>[Pd]>[OH:1][CH2:2][CH2:3][N:4]1[C:5]2[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=[CH:13][C:14]=2[N:15]=[CH:18]1

参加物

4

反応物 2

HCID 887MethanolHCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

生成物 1

HCID 11229737Methyl 1-(2-hydroxyethyl)-1H-benzimidazole-7-carboxylate

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
100 °C

実験手順

Suspension of methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate (3.06 g, 12.7 mmol) in methanol (130 mL) was hydrogenated at atmospheric pressure over 10% palladium on activated charcoal for 10 min. The mixture was filtered through a pad of Celite and the solvent was removed in vacuum. The residue was dissolved in formic acid (60 mL) and heated at 100° C. for 45 min and then kept at ambient temperature overnight. Excess of the formic acid was removed under reduced pressure. The residue was dissolved in methanol (100 mL) and treated with concentrated ammonia in methanol (20 mL) for 50 min followed by evaporation of the volatiles. Purification by column chromatography on silica using dichloromethane in methanol 95:5 afforded methyl 1-(2-hydroxyethyl)-1H-benzimidazole-7-carboxylate, 2.31 g (83%). %). MS (ESI) m/z 221 [M+H]. 1H NMR (400 MHz, CD3OD) δ ppm 3.78 (t, J=5.05 Hz, 2H), 3.96 (s, 3H), 4.70 (t, J=5.05 Hz, 2H), 7.33 (t, J=7.83 Hz, 1H), 7.84-7.91 (m, 2H), 8.20 (s, 1H).

後処理

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe solvent was removed in vacuum
  3. dissolutionThe residue was dissolved in formic acid (60 mL)
  4. customExcess of the formic acid was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (100 mL)
  6. additiontreated with concentrated ammonia in methanol (20 mL) for 50 min
  7. customfollowed by evaporation of the volatiles
  8. customPurification by column chromatography on silica

出典と根拠

ORDレコード
ord-86af66fcc24e40118243bc78edb3c58c
出典データセット
uspto-grants-2010_01
特許番号
US07645784B2

反応ノート

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