Ethyl Acetate → HCID 15296707, compound

HRID 1647862Notes

Reaction equation

HRID 1647862 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:19]([OH:21])=O)[CH3:3].C1N=C[N:24](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-].C(OCC)(=O)C>C1COCC1>[CH3:1][CH:2]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:19]([NH2:24])=[O:21])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 14256757HCID 14256757, compound

Product 1

HCID 15296707HCID 15296707, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 1,7-bis-(1-methylethoxy)-2-naphthalenecarboxylic acid (200 mg, 0.69 mmol) in 10 mL of THF is added N,N-carbonyldiimidazole (135 mg, 0.83 mmol). The solution is heated at reflux for 1 hour and cooled to room temperature. Aqueous NH4OH (4 mL) is added and the reaction mixture is stirred at room temperature for 30 minutes, then poured into ethyl acetate, and washed with aqueous NaHCO3 and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is recrystallized from methanol and water to provide 1,7-bis-(1-methylethoxy)-2-naphthalenecarboxamide in 40% yield; mp 145°-146° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. washwashed with aqueous NaHCO3 and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is recrystallized from methanol and water

Sources & evidence

ORD record
ord-1132ca12710546c681b62c532e27657c
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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