Sodium Carbonate → Pyrrole-2-carboxaldehyde

HRID 414596

반응식

HRID 414596 반응식
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:8]([N:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1)[C:9]1C=CN=CC=1)[CH3:7].O.O.O.[C:23]([O-:26])(=[O:25])[CH3:24].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C.O.CN(C)C=O>[NH:15]1[CH:16]=[CH:17][CH:18]=[C:19]1[CH:23]=[O:25].[NH:8]1[CH:6]=[CH:7][C:24]([CH:23]=[O:26])=[CH:9]1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 10845273HCID 10845273, 화합물HCID 23665404Sodium Acetate Trihydrate

생성물 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 6403081H-pyrrole-3-carboxaldehyde

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 63651,1-Dichloroethane용매

실험 절차

To cold dimethylformamide (11.1 g) was slowly added phosphorous oxychloride (23.2 g). The resultant clear complex was stirred one hour at ambient temperature and thereafter a solution of N-ethyl-N-(1H-pyrrol-1-yl)-4-pyridinamine (20.5 g) in 135 ml of dichloroethane was added. After stirring twelve hours at 95° the reaction mixture was cooled and hydrolyzed for one hour at 95° with a solution of sodium acetate trihydrate (40 g) in 150 ml of water. The reaction mixture was cooled, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution and thereafter dried over anhydrous magnesium sulfate, filtered and evaporated to 24 g of an oil. This oil was purified first by flash chromatography (silica, dichloromethane, then 10% ethyl acetate in dichloromethane), then by high-pressure liquid chromatography (silica, ethyl acetate) to give 8 g of the pyrrole-2-aldehyde as an oil and 8 g of the pyrrole-3-aldehyde as an oil. 2.5 g of the pyrrole-2-aldehyde was converted to the hydrochloride salt in 2-propanol to give 2.2 g of crystals, mp 214°-215° C.

후처리

  1. stirringAfter stirring twelve hours at 95° the reaction mixture
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to 24 g of an oil
  9. customThis oil was purified first by flash chromatography (silica, dichloromethane

출처 및 근거

ORD 기록
ord-a6e98d69a462478b9e526e6b5d374456
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04792562

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