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

HRID 1486988Notes

Reaction equation

HRID 1486988 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3254ece2809848ba8b9bb14ca85fddf6
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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