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

HRID 1716610Notes

Reaction equation

HRID 1716610 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-a7b023ae4e16457193e5b0e8cb200531
Source dataset
uspto-grants-2010_09
Patent number
US07803828B2

Reaction notes

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