Sodium Hydroxide → CID 136342890

HRID 869481

Reaction equation

HRID 869481 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH:11]=O)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[NH2:14][OH:15].[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[C:3]2[C:10]([CH:11]=[N:14][OH:15])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 567638284-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde

Product 1

HCID 136342890CID 136342890Yield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (1.17 g, 6.47 mmol, 1.0 eq) and hydroxylamine hydrochloride (0.54 g, 7.77 mmol, 1.2 eq) in EtOH (25 mL), aqueous NaOH solution (0.31 g, 7.77 mmol, 1.2 eq) in H2O (4 mL) was added dropwise. The resulting mixture was stirred at RT for 30 min and then was diluted with a sufficient amount of EtOH to allow stirring for additional 30 min. The solid was collected by filtration, rinsed with H2O and dried in vacuo to afford 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (0.89 g, 70% yield) as a mixture of isomers. ESI-MS m/z: 194.8 [M−H]−.

Workup

  1. additionwas added dropwise
  2. stirringto allow stirring for additional 30 min
  3. filtrationThe solid was collected by filtration
  4. washrinsed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-156c90d4d22747109081027bf45a25b6
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Linked notes

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