Water → Methyl 6-cyanonaphthalene-2-carboxylate

HRID 1384180Notes

Reaction equation

HRID 1384180 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2)=O.O>P(OC)(OC)(OC)=O>[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2)#[N:1]

Participants

4

Reactant 2

HCID 962WaterHCID 12052259Methyl 6-carbamoylnaphthalene-2-carboxylate

Product 1

HCID 12433083Methyl 6-cyanonaphthalene-2-carboxylateYield 92.2%

Reagents, catalysts & solvents 1

HCID 10541Trimethyl PhosphateSolvent

Procedure

A suspension of Example 8C (31 g, 135 mmole) in trimethyl phosphate (450 mL) was treated with triphosgenie (27 g, 136 mmole), stirred for 20 min at room temperature and heated in an oil bath at 80° C. for 1 h. The product precipated from the solution while cooling to room temperature. The thick slutty was treated with water and filtered, and the white solid was thoroughly washed with water and dried under vacuum to provide 26.3 g of the title compound.

Workup

  1. temperatureheated in an oil bath at 80° C. for 1 h
  2. temperaturewhile cooling to room temperature
  3. filtrationfiltered
  4. washthe white solid was thoroughly washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0451636f8f8d4306959f9c1d0faf37c7
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

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