Methanol → 2,3-Dihydro-1H-indole-6-carbonitrile

HRID 1674487Notes

Reaction equation

HRID 1674487 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+].CO>O1CCOCC1>[C:13]([C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][CH2:5][NH:4]2)=[CH:8][CH:9]=1)#[N:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 673179911-Acetylindoline-6-carbonitrile

Product 1

HCID 162444472,3-Dihydro-1H-indole-6-carbonitrileYield 51.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Acetyl-6-cyanoindoline (2.4 g, 12.9 mmol, Tetrahedron, 1967, 23, 3823) was stirred in a solution containing 5 N NaOH (20 mL), MeOH (60 mL) and dioxane (60 mL). The mixture was stirred at RT over the weekend. Solvent was removed under reduced pressure and the residue was partitioned between water (100 mL) and DCM (100 mL). Aqueous layer was extracted with DCM (2×75 mL). Combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. Chromatography (10-30% EtOAc/hexanes) provided 6-cyanoindoline (0.95 g, 51%) which was then converted to 12A in a manner similar to that found in Example 4, Step 1.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was partitioned between water (100 mL) and DCM (100 mL)
  3. extractionAqueous layer was extracted with DCM (2×75 mL)
  4. dry with materialCombined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-904e86492f6941019926e9ffb11e2fde
Source dataset
uspto-grants-2011_08
Patent number
US08003624B2

Reaction notes

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