Diethylamine → 6-(Diethylaminocarbonyl)-2-naphthalenecarboxylic acid

HRID 1636378Notes

Reaction equation

HRID 1636378 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([OH:25])=O)=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:26]([OH:28])=[O:27].OC1C2N=NNC=2C=CC=1.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40]>CN(C)C=O>[CH2:39]([N:41]([CH2:42][CH3:43])[C:23]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH:13]=[C:14]([C:26]([OH:28])=[O:27])[CH:15]=[CH:16]2)=[O:25])[CH3:40]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 143572,6-Naphthalenedicarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 193511076-(Diethylaminocarbonyl)-2-naphthalenecarboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (22.2 g, 115 mmol) was added to a solution of 2,6-naphthalenedicarboxylic acid (25 g, 115 mmol) and hydroxybenzotriazole (15.6 g, 115 mmol) in dimethylformamide (1800 ml) and the mixture was stirred at room temperature for 2 hours. Diethyl amine (34.3 ml, 345 mmol) was added and the solution was stirred overnight at room temperature. The solvent was then evaporated under reduced pressure and the crude was treated with 1N HCl (500 ml) and ethyl acetate (500 ml), insoluble compounds were filtered off and the phases were separated. The organic phase was extracted with 5% sodium carbonate (3×200 ml) and the combined aqueous solutions were acidified with concentrated HCl and extracted with ethyl acetate (3×200 ml). The organic solution was then washed with 1N HCl (6×100 ml), dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure yielding 18.5 g (Yield 60%) of pure 6-(diethylaminocarbonyl)-2-naphthalenecarboxylic acid; m.p.=122-124° C.

Workup

  1. stirringthe solution was stirred overnight at room temperature
  2. customThe solvent was then evaporated under reduced pressure
  3. additionthe crude was treated with 1N HCl (500 ml) and ethyl acetate (500 ml), insoluble compounds
  4. filtrationwere filtered off
  5. customthe phases were separated
  6. extractionThe organic phase was extracted with 5% sodium carbonate (3×200 ml)
  7. extractionextracted with ethyl acetate (3×200 ml)
  8. washThe organic solution was then washed with 1N HCl (6×100 ml)
  9. dry with materialdried over anhydrous sodium sulphate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-74c56e0b43924e46a3ad9b1bd35fbb11
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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