Water → Methyl 3-amino-5-(hydroxymethyl)benzoate

HRID 49313

Reaktionsgleichung

Reaktionsgleichung von HRID 49313
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=1)[C:7](O)=[O:8])([O-])=O.O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[NH2:1][C:4]1[CH:12]=[C:11]([CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=1)[C:13]([O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

Produkt 1

HCID 10535399Methyl 3-amino-5-(hydroxymethyl)benzoateAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

85 g of 3-nitro-5-methoxycarbonylbenzoic acid was dissolved in 200 ml of THF under a flow of nitrogen, and 43.4 ml of borane dimethylsulfide complex was added with stirring under ice-cooling. After stirring for 18 hours, 200 ml of water was added, and then 96 g of potassium carbonate was added. It was extracted with ethyl acetate, and theorganic layer was washed with salt solution. After drying with magnesium sulfate, the resulting solid was dissolved in 800 ml of ethyl acetate, 750 mg of 10% Pd/C was added, and stirring was continued under the flow of hydrogen. After the reaction was completed, it was subjected to the filtration, and then the filtrate was concentrated to produce 64 g of the title compound.

Aufarbeitung

  1. additionwas added
  2. temperaturecooling
  3. stirringAfter stirring for 18 hours
  4. extractionIt was extracted with ethyl acetate, and theorganic layer
  5. washwas washed with salt solution
  6. dry with materialAfter drying with magnesium sulfate
  7. dissolutionthe resulting solid was dissolved in 800 ml of ethyl acetate
  8. addition750 mg of 10% Pd/C was added
  9. stirringstirring
  10. filtrationit was subjected to the filtration
  11. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-39ab0bf8396c4e4589cc7a8137c09994
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706745B1

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