4-Chloro-3-nitrotoluene → 3-[(4-Methyl-2-nitrophenyl)amino]-1-propanol

HRID 46845

Reaktionsgleichung

Reaktionsgleichung von HRID 46845
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(O)CCC>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Komponenten

4

Edukt 2

HCID 69764-Chloro-3-nitrotolueneHCID 90863-Amino-1-propanol

Produkt 1

HCID 203855403-[(4-Methyl-2-nitrophenyl)amino]-1-propanolAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 171 parts of 1-chloro-4-methyl-2-nitrobenzene, 150 parts of 3-amino-1-propanol and 400 parts of butanol is stirred and refluxed for 30 hours. The reaction mixture is evaporated and the residue is poured onto water. The product is extracted with methylbenzene. The extract is washed with water and with a hydrochloric acid solution 2 N, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 70 parts (33%) of 3-[(4-methyl-2-nitrophenyl)amino]-1-propanol as a residue.

Aufarbeitung

  1. temperaturerefluxed for 30 hours
  2. customThe reaction mixture is evaporated
  3. additionthe residue is poured onto water
  4. extractionThe product is extracted with methylbenzene
  5. washThe extract is washed with water and with a hydrochloric acid solution 2 N
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 5% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-76bdd6ec89af49c6892f58de07c7c478
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

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