Sodium Cyanide → HCID 13324753, compound

HRID 371502Notes

Reaction equation

HRID 371502 reaction equation
COS([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH:8]=1)(=O)=O.[C-:22]#[N:23].[Na+]>CN(C=O)C>[N:13]1([C:9]2[CH:8]=[C:7]([CH2:6][C:22]#[N:23])[CH:12]=[CH:11][CH:10]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 54195974HCID 54195974, compound

Product 1

HCID 13324753HCID 13324753, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.2 g (ca. 33.8 mmole) of 3-(1-indolinyl)benzenemethanesulfonic acid methyl ester of Example 20c and 4.97 g (101.4 mmole, 3.0 equiv.) sodium cyanide in 200 ml sieve dried DMF was heated at 60°-70° C. for 50 minutes. The product was concentrated under high vacuum at 50°-60° C. and the residue was partitioned between chloroform (200 ml) and water (200 ml). The organic portion was washed twice with 200 ml water, 200 ml brine, dried over Na2SO4 and concentrated under vacuum to give 6.39 g (80.7%) of product. Kugelrohr distillation of a 0.8 g sample gave 0.6 g of an oil of 3-(1-indolinyl)benzeneacetonitrile, b.p. 189°-192° C./0.15 mm.

Workup

  1. temperaturewas heated at 60°-70° C. for 50 minutes
  2. concentrationThe product was concentrated under high vacuum at 50°-60° C.
  3. customthe residue was partitioned between chloroform (200 ml) and water (200 ml)
  4. washThe organic portion was washed twice with 200 ml water, 200 ml brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-79f0d4a2cd8a423ab2b0082de242bec6
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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