Methanol → HCID 21701976, compound

HRID 1596442Notes

Reaction equation

HRID 1596442 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10]C)=O)#[N:2].[C-]#N.[Na+].CO.[CH:19]([NH2:22])([CH3:21])[CH3:20]>CS(C)=O>[CH:19]([NH:22][C:8](=[O:10])[C:7]1[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[OH:13])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 8929Sodium CyanideHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 21701976HCID 21701976, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-cyano-2-hydroxybenzoate (8.85 g; 50 mmol; see Example 10(b) above) and NaCN (250 mg; 5 mmol) were dissolved in DMSO (10 mL) and MeOH (50 mL) and iso-propyl amine (25 mL) was added. The reaction mixture was heated (60° C. ) in a sealed steel vessel for 10 h, the MeOH was removed under reduced pressure and H2O (500 mL) was added. The solution was acidified with HCl (pH 1), filtered and the precipitate was washed with H2O giving the sub-title compound in a 93% yield.

Workup

  1. customthe MeOH was removed under reduced pressure and H2O (500 mL)
  2. additionwas added
  3. filtrationfiltered
  4. washthe precipitate was washed with H2O giving the sub-title compound in a 93% yield

Sources & evidence

ORD record
ord-248fbf37e5b343d5b5affe5052047931
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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