Hexane → HCID 15296709, compound

HRID 1647864Notes

Reaction equation

HRID 1647864 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:15]([OH:17])=O.C1N=C[N:20](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-].CCCCCC>C1COCC1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:15]([NH2:20])=[O:17]

Participants

6

Reactant 4

HCID 8058HexaneHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 142567611,7-Dimethoxy-2-naphthalenecarboxylic acid

Product 1

HCID 15296709HCID 15296709, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 1,7-dimethoxy-2-naphthalenecarboxylic acid (131 mg, 0.56 mmol) in 3 mL of THF is added N,N-carbonyldiimidazole (105 mg, 0.65 mmol). The solution is heated at reflux for 2.5 hours and cooled slightly. Aqueous NH4OH (1 mL) is added and the reaction mixture is stirred at room temperature for 1.5 hours, then poured into 1:1 hexane:ethyl acetate and washed with brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (1:1) to provide 1,7-dimethoxy-2-naphthalenecarboxamide in 49% yield; mp 134°-136° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturecooled slightly
  4. washethyl acetate and washed with brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-47bfd8afe34747058d272da1e02ca0d6
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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