p-Toluenesulfonic acid monohydrate → Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

HRID 551025ノート

反応式

HRID 551025 の反応式
[N+:1]([C:4]1[C:12]2[N:11]([CH2:13][C:14](OC)=[O:15])[C:10](=[O:18])[N:9]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pd]>[O:18]=[C:10]1[N:11]2[CH2:13][C:14](=[O:15])[NH:1][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([C:12]=32)[N:9]1[CH2:19][C:20]([O:22][CH3:23])=[O:21]

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66636623Dimethyl 2,2'-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate

生成物 1

HCID 86629734Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of dimethyl 2,2′-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate from Step B (270 mg, 0.84 mmol) and 10% Pd/C (50 mg) in MeOH (100 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm). After 2 h, the reaction was filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in toluene (3 mL) and p-toluenesulfonic acid monohydrate (2 mg, 0.011 mmol) was added. The mixture was heated at reflux for 30 min and then concentrated in vacuo to give the title compound. MS: m/z=262 (M+1).

後処理

  1. filtrationthe reaction was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude solid was dissolved in toluene (3 mL)
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 30 min
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-115af42059114480b545d35df31d2e4e
出典データセット
uspto-grants-2011_05
特許番号
US07947677B2

反応ノート

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