Triethylamine → 4-Amino-1-naphthoic acid

HRID 49932

Reaction equation

HRID 49932 reaction equation
C(N(CC)CC)C.NC1C2C(=CC=CC=2)C(Br)=CC=1.[OH-].[Na+].[NH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33]([O:35]C)=[O:34])=[CH:25][CH:24]=1>[C]=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C.CN(C)C=O.CO>[NH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33]([OH:35])=[O:34])=[CH:25][CH:24]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 753034-Bromo-1-naphthylamineHCID 10821944Methyl 4-aminonaphthalene-1-carboxylate

Product 1

HCID 4593144-Amino-1-naphthoic acid

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 178418416HCID 178418416, compoundSolvent

Conditions

Temperature
80 °C

Procedure

1.60 g (2.3 mmol) of bis(triphenylphosphine)dichloropalladium, 7.0 ml (50.6 mmol) of triethylamine and 60 ml of methanol were successively added to a mixture of 5.00 g (22.5 mmol) of 1-amino-4-bromonaphthalene and 60 ml of dimethylformamide, and they were stirred in carbon monoxide atmosphere at 80° C. for 2 days. After the concentration under reduced pressure, water was added to the reaction mixture and the product was extracted with ethyl acetate and concentrated. 20 ml of ethanol and 10 ml (40.0 mmol) of 4 N aqueous sodium hydroxide solution were added to crude methyl 4-amino-1-naphthalenecarboxylate thus obtained. They were stirred at 80° C. overnight. Ethanol was evaporated, and the residue was washed with ethyl acetate. The aqueous layer was neutralized with hydrochloric acid. After the extraction with ethyl acetate, the product was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound.

Workup

  1. concentrationAfter the concentration under reduced pressure, water
  2. additionwas added to the reaction mixture
  3. extractionthe product was extracted with ethyl acetate
  4. concentrationconcentrated
  5. customthus obtained
  6. customEthanol was evaporated
  7. washthe residue was washed with ethyl acetate
  8. extractionAfter the extraction with ethyl acetate
  9. washthe product was washed with water and saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5698eedece90432c9b83a625bb4512b2
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Linked notes

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