Ammonia → (5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

HRID 1486988노트

반응식

HRID 1486988 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=O)[CH2:8][CH2:9][C:2]=12.[OH2:11].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:20]O.N>CCO.ClCCl.CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2/[C:7](=[N:20]\[OH:11])/[CH2:8][CH2:9][C:2]=12

참가 물질

9

반응물 4

HCID 222AmmoniaHCID 443297Hydroxyamine hydrochlorideHCID 15125216,7-Dihydro-5H-1-pyridin-5-oneHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 45079548(5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine수율 94.4%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

In a 100-mL, 3N round-bottomed flask 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one (2.0 g, 1.0 eq.) was dissolved in EtOH (24.0 mL) and H2O (6.0 mL) at RT. Then Sodium acetate trihydrate (8.175 g, 4.0 eq.) and Hydroxylamine hydrochloride (4.174 g, 4.0 eq.) were added at the same temperature. The progress of the reaction was followed by TLC analysis on TLC with 5% Methanol: dichloromethane with ammonia atmosphere as mobile phase and visualization with U.V light. The reaction mixture was quenched in 50 mL water and extracted by dichloromethane. Organic layer was concentrated by rotary evaporation (35° C., 20 mmHg) to afford 2.10 g of crude compound which was used in the next step without purification.

후처리

  1. customat RT
  2. customThe reaction mixture was quenched in 50 mL water
  3. extractionextracted by dichloromethane
  4. concentrationOrganic layer was concentrated by rotary evaporation (35° C., 20 mmHg)

출처 및 근거

ORD 기록
ord-3254ece2809848ba8b9bb14ca85fddf6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428490B2

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