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Hydroxyamine hydrochloride → 2-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde oxime hydrochloride

HRID 1646237
Notes
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Reaction equation

HRID 1646237 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:18].[NH2:19][OH:20]>C(O)C>[ClH:18].[C:1]1([C:7]2[C:15]([CH:16]=[N:19][OH:20])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 151581792-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde

Product 1

HCID 867439182-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde oxime hydrochlorideYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde (0.5 g) and hydroxylamine.hydrochloride (0.17 g) in ethanol (5 ml) was refluxed for 1.5 hours and evaporated in vacuo. The residue was triturated with ethyl acetate and recrystallized from a mixture of ethanol and ethyl acetate to give 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde oxime hydrochloride (0.28 g).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. customevaporated in vacuo
  3. customThe residue was triturated with ethyl acetate
  4. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-6efa50fe8e4246b898e3a25b674b3132
Source dataset
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05179103

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes