Ammonium Hydroxide → HCID 9795138, compound

HRID 1647858Notes

Reaction equation

HRID 1647858 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([OH:19])=O)=[C:10]2[O:13][CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1.C1N=C[N:22](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:17]([NH2:22])=[O:19])=[C:10]2[O:13][CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 14256756HCID 14256756, compound

Product 1

HCID 9795138HCID 9795138, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (141 mg, 0.54 mmol) in 10 mL of THF is added N,N-carbonyldiimidazole (105 mg, 0.65 mmol). The solution is heated at reflux for 1 hour and cooled slightly. Aqueous NH4OH (2.5 mL) is added and the reaction mixture is stirred at room temperature for 40 minutes then partitioned between 1:1 hexane:ethyl acetate and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is recrystallized from hexane and ethyl acetate to provide 7-methoxy-1-(1 methylethoxy)-2-naphthalenecarboxamide in 68% yield; mp 172°-174° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled slightly
  4. customthen partitioned between 1:1 hexane
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is recrystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-72a429ec9146498593ea10c4f2696d5e
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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