Sodium Hydroxide → CID 136342890

HRID 1910870Notes

Reaction equation

HRID 1910870 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 136342890

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (E-3) (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) is added dropwise. The resulting mixture is stirred at RT for 30 min and then is diluted with a sufficient amount of EtOH to allow stirring for additional 30 min. The solid is collected by filtration, rinsed with H2O and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (E-4) as a mixture of isomers.

Workup

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

Sources & evidence

ORD record
ord-157457a88ec04b87bc619ce7edb67eed
Source dataset
uspto-grants-2013_12
Patent number
US08604032B2

Reaction notes

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