Hydroxyamine hydrochloride → 6-Bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde oxime

HRID 1253458Notes

Reaction equation

HRID 1253458 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[CH:11]=O)[CH:7]=1.Cl.[NH2:16][OH:17].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[CH:11]=[N:16][OH:17])[CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 86583087HCID 86583087, compound

Product 1

HCID 866570506-Bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde (100 mg, 0.365 mmol), hydroxylamine hydrochloride (27.9 mg, 0.401 mmol) and sodium bicarbonate (33.7 mg, 0.401 mmol) were suspended in absolute ethanol (4 ml) and stirred for 1 h (heavy colorless precipitate forms). The mixture was concentrated to dryness, then diluted in 8 mL of water and stirred for 5 minutes. The solid was filtered, washed with water, then placed under vacuum overnight to afford 6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde oxime as a mixture of oxime isomers.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted in 8 mL of water
  3. stirringstirred for 5 minutes
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customplaced under vacuum overnight

Sources & evidence

ORD record
ord-cefa9ee4f86e460f81fa34f1c6e016dc
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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