Ethanol → HCID 18368010, compound

HRID 379830Notes

Reaction equation

HRID 379830 reaction equation
C([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18](C#N)[CH:17]=1)(=O)C.[OH-:25].[K+].[CH2:27]([OH:29])C>O>[NH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:27]([OH:29])=[O:25])[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 18367973HCID 18367973, compound

Product 1

HCID 18368010HCID 18368010, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-acetylamino-6-chloro-2-(3-cyanobenzoyl)indole (Example 130, 2.7 g, 7.99 mmol) and potassium hydroxide (2.2 g, 40 mmol) in ethanol (100 ml) and water (100 ml) was heated at reflux for 5 h. The mixture was cooled and concentrated, and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous layer was separated and acidified with 2N aqueous hydrochloric acid, extracted with ethyl acetate (100 ml×2) and the combined extracts dried (MgSO4). After removal of solvent the residual solids were recrystallization from ethyl acetate to afford 1.8 g (72%) of the title compound as brown solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate (100 ml×2)
  8. dry with materialthe combined extracts dried (MgSO4)
  9. customAfter removal of solvent the residual solids
  10. customrecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-81284a757c6a4295bd899bc8620e8f71
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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