Pyridine → HCID 86651036, compound

HRID 518180Notes

Reaction equation

HRID 518180 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][C:22](=O)[C:21]3[C:16](=[CH:17][CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][OH:30])=[O:28])[CH:20]=3)[O:15]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:31][O:32][CH3:33].Cl.N1C=CC=CC=1>CCO>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][C:22](=[N:31][O:32][CH3:33])[C:21]3[C:16](=[CH:17][CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][OH:30])=[O:28])[CH:20]=3)[O:15]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 52951036HCID 52951036, compound

Product 1

HCID 86651036HCID 86651036, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (E)-3-{1′-benzyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide hydrochloride (150 mg, 0.35 mmol), NH2OCH3.HCl (63.5 mg, 0.76 mmol) and pyridine (61 μl, 0.70 mmol) in EtOH (10 ml) was heated to reflux. After 2 h, the solution was evaporated under vacuum. The crude residue was triturated with Et2O/H2O 90/10 to give (E)-3-{1′-benzyl-4-methyloxyimino-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide (150 mg) as a 90/10 mixture of the two isomers (hydrochloride salts).

Workup

  1. temperaturewas heated to reflux
  2. customthe solution was evaporated under vacuum
  3. customThe crude residue was triturated with Et2O/H2O 90/10

Sources & evidence

ORD record
ord-31877f27f3ac41599a9e319ff8dbd2cf
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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