Hydrochloric Acid → 4-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

HRID 1750248

Reaktionsgleichung

Reaktionsgleichung von HRID 1750248
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH2:29])[CH3:22].Cl>O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:29][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]2[CH2:21][CH3:22])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5448542-Ethylcyclohexan-1-amineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Produkt 1

HCID 867144554-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.48 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 1.5 ml of abs. DMF was added 1.00 g of potassium carbonate, followed by 0.31 g of 2-ethylcyclohexylamine. After 16 h at rt, the mixture was poured into water, the pH was adjusted to 4 by the addition of 2 M aqueous hydrochloric acid, and the reaction mixture was extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over sodium sulphate and concentrated to yield 0.44 g (60%) of 4-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate three times
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b829104c944846b0bb6b409d8ee258e9
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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