Acetaldehyde → Methyl 4-cyano-2-(ethylamino)benzoate

HRID 1442579ノート

反応式

HRID 1442579 の反応式
[CH:1](=O)[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:18][C:19]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])O.[Na+]>C(O)(=O)C>[C:29]([C:27]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([NH:18][CH2:1][CH3:2])[CH:28]=1)#[N:30]

参加物

6

反応物 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10103677Benzoic acid, 2-amino-4-cyano-, methyl ester

生成物 1

HCID 23076867Methyl 4-cyano-2-(ethylamino)benzoate収率 23%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Acetaldehyde (90%)(10 mL) and sodium triacetoxyborohydride (7.71 g, 36.4 mmol) were added to an acetic acid solution (10 mL) of methyl 2-amino-4-cyanobenzoate (3.04 g, 17.3 mmol) under ice cooling. The mixture was stirred at the same temperature for an hour and at room temperature for 2 hours. Ice water was added to the reaction mixture, the mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. The combined organic layers were washed with water and then saturated brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crystals obtained were washed with diisopropyl ether-hexane to give the title compound (800 mg, 23%). The residue was applied to silica gel column chromatography (hexane/ethyl acetate=50:1 and then 30:1). The crystals obtained were washed with hexane to give the title compound (920 mg, 26%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialsaturated brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crystals obtained
  7. washwere washed with diisopropyl ether-hexane

出典と根拠

ORDレコード
ord-74a073dbcb8f45c58f6674ad07984e17
出典データセット
uspto-grants-2010_02
特許番号
US07659267B2

反応ノート

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