Potassium Cyanide → Benzoic acid, 2-(cyanomethyl)-6-nitro-, methyl ester

HRID 511367Notes

Reaction equation

HRID 511367 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>O.CO>[C:1]([CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 19701861Benzoic acid, 2-(cyanomethyl)-6-nitro-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of KCN (474 mg, 7.2 mmol) in water (1 mL) was slowly added to a solution of methyl 2-(bromomethyl)-6-nitrobenzoate (1 g, 3.6 mmol) in methanol (20 mL). This mixture was allowed to stir for 4 h at 50° C. The reaction mixture was concentrated to remove methanol, diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried (Na2SO4), concentrated and purified by flash column chromatography (25% EtOAc in hexanes) to give the title compound as 0.5 g of an oily liquid (62%). 1H NMR (CDCl3, 600 MHz): δ 3.9 (s, 2H), 3.97 (s, 3H), 7.65 (t, J=7.8 Hz, 1H), 7.85 (d, J=7.8 Hz, 1H), 8.09 (d, J=7.8 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove methanol
  3. additiondiluted with water (20 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-894ae652b45a428fb794e0ca41c9b9d9
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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