2-(6-methoxynaphthalen-2-yl)prop-2-enoic Acid → Naproxen

HRID 1088491Notes

Reaction equation

HRID 1088491 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.C1(C(N)C2CCCCC2)CCCCC1.[H][H]>CO>[CH3:17][C@H:13]([C:14]([OH:16])=[O:15])[C:8]1[CH:7]=[CH:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 37179052-(6-methoxynaphthalen-2-yl)prop-2-enoic AcidHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 156391NaproxenYield 84.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml autoclave, the inside atmosphere of which had previously been replaced with argon, were placed 0.45 g (2 mmoles) of 6-methoxy-α-methylene-2-naphthaleneacetic acid, 20 ml of methanol, and 0.39 g (2 mmoles) of dicyclohexylmethylamine. Then, 9.0 mg (0.010 mmole) of Ru((-)-T-BINAP)(O2CCH3)2 prepared according to the same manner as in Referential Example 3 except using (-)-T-BINAP in place of (-)-BINAP was added to the mixture to perform hydrogenation for 12 hours at a hydrogen pressure of 135 kg/cm2 and at a reaction temperature of 17° C. Thereafter, the solvent was distilled off to provide 0.39 g of naproxen. The yield was 84%.

Workup

  1. additionwas added to the mixture
  2. customfor 12 hours
  3. customat a reaction temperature of 17° C
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-3f9404edda72439dad9694210e9701fc
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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