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

HRID 1442579노트

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HRID 1442579 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-74a073dbcb8f45c58f6674ad07984e17
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659267B2

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