Sodium Hydroxide → HCID 57985931, compound

HRID 1869201Notes

Reaction equation

HRID 1869201 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]1[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])C.[OH-].[Na+]>CCO>[C:21]1([CH:11]([C:12]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[NH:14][CH:13]=2)[CH:5]([C:4]([OH:27])=[O:3])[C:6]([OH:8])=[O:7])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57985923HCID 57985923, compound

Product 1

HCID 57985931HCID 57985931, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a RT solution of 2-[phenyl-(1H-pyrrolo[3,2-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.77 g) in EtOH (40 mL) was added NaOH (2 M in water, 15 ml). The mixture was stirred at reflux for 5 h, cooled to RT, and concentrated. The aqueous residue was acidified by addition of HCl (1 M) until dissolution. To this solution was added EtOAc resulting in precipitation of a solid, which was collected by filtration and dried, affording 2-[Phenyl-(1H-pyrrolo[3,2-c]pyridin-3-yl)-methyl]-malonic acid (341 mg, 52% yield).

Workup

  1. temperatureat reflux for 5 h
  2. concentrationconcentrated
  3. additionThe aqueous residue was acidified by addition of HCl (1 M) until dissolution
  4. additionTo this solution was added EtOAc resulting
  5. customin precipitation of a solid, which
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-45eee84b3566444a8d35b852b28d7632
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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