Butylamine → 4-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

HRID 1973107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973107
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21].C(NC1C=C(Cl)NC(C)([N+]([O-])=O)C=1C(OCC)=O)CCC>CO.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 8007ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylateHCID 867342334-Butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester

Produkt 1

HCID 123875984-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

139.5 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.5 Mol.) are dissolved in about 500 ml. of methanol. 60 g. of triethylamine are added and the solution is heated at reflux temperature. At this point, 36.5 g. of n-butylamine are added dropwise. The solvent is then removed in vacuo and 500 ml. of benzene are added to the residue. The triethylamine hydrochloride is filtered off and the solvent evaporated. The resulting oil is dissolved in 300 ml. of methanol and yields on cooling 110 g. of 4-butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester (70%), m.p. 33°-35° (methanol).

Aufarbeitung

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. customThe solvent is then removed in vacuo and 500 ml
  4. additionof benzene are added to the residue
  5. filtrationThe triethylamine hydrochloride is filtered off
  6. customthe solvent evaporated
  7. dissolutionThe resulting oil is dissolved in 300 ml
  8. customof methanol and yields
  9. temperatureon cooling 110 g

Quellen und Nachweise

ORD-Eintrag
ord-2c88c7993f9b4719be9f08060b9f5eec
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03996233

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