Ethylamine → HCID 10565212, compound

HRID 1647859Notes

Reaction equation

HRID 1647859 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.[CH:20]1N=C[N:22](C(N2C=NC=C2)=O)[CH:21]=1.C(N)C>C1COCC1>[CH2:21]([NH:22][C:17]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]=1[O:13][CH:14]([CH3:15])[CH3:16])=[O:19])[CH3:20]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14256756HCID 14256756, compound

Product 1

HCID 10565212HCID 10565212, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (200 mg, 0.77 mmol in 5 mL of THF is added N,N-carbonyldiimidazole (162 mg, 1.00 mmol). The solution is heated at reflux for 1 hour and cooled slightly. Ethylamine (0.44 mL of a 70% aqueous solution) is added and the reaction mixture is stirred at room temperature for 30 minutes, followed by partitioning between ethyl acetate, and 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 (2:1) to provide N-ethyl-7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxamide in 70% yield; mp 78°-79° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled slightly
  4. customby partitioning between ethyl acetate, and 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 (2:1)

Sources & evidence

ORD record
ord-2f9e5a28ef2f4b0d99e574544c35f444
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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