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

HRID 1486988ノート

反応式

HRID 1486988 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3254ece2809848ba8b9bb14ca85fddf6
出典データセット
uspto-grants-2016_08
特許番号
US09428490B2

反応ノート

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