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

HRID 981947
Notes
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Reaction equation

HRID 981947 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-9adf7bc89ce3430daf5f3be9797cfac1
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04994453

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes