Hydrochloric Acid → HCID 117770785, compound

HRID 1526401Notes

Reaction equation

HRID 1526401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[C:4](=[O:13])[C:3]=1[CH:14]=O.Cl.[NH2:17][OH:18].Cl>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[C:4](=[O:13])[C:3]=1[CH:14]=[N:17][OH:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 117770640HCID 117770640, compound

Product 1

HCID 117770785HCID 117770785, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-1-((2S)-3-methylbutan-2-yl)-2-oxo-1,2-dihydropyridine-3-carbaldehyde obtained in Step C (31.8 g) in 2-propanol (300 mL) were added hydroxylamine hydrochloride (14.6 g) and conc. hydrochloric acid (0.43 mL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was crystallized from (2-propanol/diisopropyl ether), and the resulting solid was collected by filtration, and washed with 2-propanol/diisopropyl ether to give the title compound (23.2 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was crystallized from (2-propanol/diisopropyl ether)
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with 2-propanol/diisopropyl ether

Sources & evidence

ORD record
ord-afbce446c8c24ed0816d98b646f9d18e
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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