Water → HCID 15296708, compound

HRID 1647863Notes

Reaction equation

HRID 1647863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH:14]([CH3:16])[CH3:15])=[C:8]([C:17]([OH:19])=O)[CH:7]=[CH:6]2.C(Cl)(=O)C(Cl)=O.[NH4+:26].[OH-].O>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH:14]([CH3:16])[CH3:15])=[C:8]([C:17]([NH2:26])=[O:19])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 14256753HCID 14256753, compound

Product 1

HCID 15296708HCID 15296708, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To an ice water cooled solution of 6-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (5.0 g, 19 mmol) in 50 mL of THF is added 2 drops of DMF followed by oxalyl chloride (2.8 g, 21 mmol). The solution is stirred a room temperature for 2 hours then poured onto 150 mL of aqueous NH4OH. An additional 700 mL of water is added and the resultant precipitate collected. Recrystallization from ethyl acetate provides 6-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxamide in 74% yield; mp 183°-184° C.

Workup

  1. customthe resultant precipitate collected
  2. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-85b8aa4ea1e840dcbc5a2ca61295ffae
Source dataset
uspto-grants-1995_07
Patent number
US05434188

Reaction notes

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