Hydrochloric Acid → 4-(5-Chloroindol-3-yl)-2-methylamino-4oxo-2-butenoic acid

HRID 2083874Notes

Reaction equation

HRID 2083874 reaction equation
C([O:3][C:4](=[O:21])[C:5]([NH:19][CH3:20])=[CH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][CH:10]=1)=[O:8])C.[OH-].[Na+].Cl>O1CCOCC1>[Cl:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C:7](=[O:8])[CH:6]=[C:5]([NH:19][CH3:20])[C:4]([OH:21])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 600774434-(5-Chloroindol-3-yl)-2-methylamino-4-oxo-2-butenoic acid ethyl ester

Product 1

HCID 698911394-(5-Chloroindol-3-yl)-2-methylamino-4oxo-2-butenoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.22 g of the ester described in above (1) in dioxane (2.2 ml) was added 1 N NaOH (0.9 ml). After stirring for 2 hours, the mixture was treated with 1 N hydrochloric acid (0.9 ml), and concentrated under reduced pressure. The residue was diluted with water. The obtained crystal was collected by filtration, and washed with water and 95% EtOH to give 0.15 g of the titled compound. Yield: 80%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe obtained crystal was collected by filtration
  4. washwashed with water and 95% EtOH

Sources & evidence

ORD record
ord-4edbe845fd6c43a0b187d98e0723ed2c
Source dataset
uspto-grants-2004_04
Patent number
US06716605B2

Reaction notes

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