Sulfuric Acid → HCID 16638027, compound

HRID 2293541Notes

Reaction equation

HRID 2293541 reaction equation
N[C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].S(=O)(=O)(O)O.N([O-])=O.[Na+].[C-:25]#[N:26].[Na+]>O>[C:25]([C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:26]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 16638096Methyl 5-amino-2,4-dimethoxybenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 16638027HCID 16638027, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent5×

Conditions

Temperature
80 °C

Procedure

A 1.00 g portion of methyl 5-amino-2,4-dimethoxybenzoate was dissolved in 5 ml of water, 0.50 ml of concentrated sulfuric acid was added and then 356 mg of sodium nitrite dissolved in 2 ml of water was added dropwise under ice-cooling, followed by a short period of stirring. Separately, 1.00 g of cuprous cyanide was dissolved in 4 ml of water and, with ice-cooling, 2.00 g of sodium cyanide dissolved in 4 ml of water was added dropwise thereto, followed by 1 hour of stirring. This was mixed with the previously prepared solution and heated at 80° C. to effect the reaction, the resulting reaction solution was mixed with water, extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and then the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1 to chloroform:methanol=50:1) to give 0.65 g of methyl 5-cyano-2,4-dimethoxybenzoate.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. waitfollowed by a short period
  4. temperaturecooling
  5. additionwas added dropwise
  6. stirringof stirring
  7. additionThis was mixed with the previously prepared solution
  8. customthe reaction
  9. customthe resulting reaction solution
  10. extractionextracted with chloroform
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under a reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1 to chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-16c9f7974842433d9066b9d74aabc2b4
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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