2-Naphthoic acid → HCID 178522640, compound

HRID 1421925Notes

Reaction equation

HRID 1421925 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[NH2:14][C:15]1[N:19]=[CH:18][NH:17][N:16]=1>O1CCCC1>[N:17]1[N:16]=[C:15]([NH:14][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:13])[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 71232-Naphthoic acidHCID 178418311HCID 178418311, compound

Product 1

HCID 178522640HCID 178522640, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-naphthyl carboxylic acid (3.0 g, 17 mmol) and N,N'-carbonyldiimidazole (3.1 g, 19 mmol) in dry tetrahydrofuran (75 ml) was stirred at reflux temperature for 1 h. To the cooled reaction mixture was added 3-amino-1,2,4-triazole (1.5 g, 17 mmol) and the resulting mixture was refluxed for 2.5 h. The cooled reaction mixture was quenched with water (150 ml) and the precipitate was filtered off and washed with water (2×20 ml), heptane (2×20 ml) and diethyl ether (2×20 ml), dried in vacuo at 50° C. affording 2.55 g (61%) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 1 h
  2. customTo the cooled reaction mixture
  3. temperaturethe resulting mixture was refluxed for 2.5 h
  4. customThe cooled reaction mixture
  5. customwas quenched with water (150 ml)
  6. filtrationthe precipitate was filtered off
  7. washwashed with water (2×20 ml), heptane (2×20 ml) and diethyl ether (2×20 ml)
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-b6f00cd22a1b4e5bbe6531da98eb6bc2
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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