1-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride → 3-(2-Chloroethyl)-4-oxo-(1H)-cinnoline

HRID 704566

Reaktionsgleichung

Reaktionsgleichung von HRID 704566
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][Cl:13].[N:15]([O-])=O.[Na+]>Cl.O>[Cl:13][CH2:12][CH2:11][C:10]1[C:9](=[O:14])[C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:2][N:15]=1

Komponenten

5

Edukt 2

HCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 200727583-(2-Chloroethyl)-4-oxo-(1H)-cinnoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1-(2-aminophenyl)-4-chlorobutan-1-one hydrochloride (b 11.3 g, 0.0427 mol) in concentrated hydrochloric acid (1200 ml) was cooled down to 0° with stirring. Then sodium nitrite (3.54 g, 0.051mol) in water (25 ml) was added dropwise. On completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The solution was evaporated under reduced pressure to dryness. The solid obtained was washed with a solution of sodium acetate and collected by filtration to give the title compound, 5.32 g. Recrystallization from methanol gave the product, m.p. 201-203°.

Aufarbeitung

  1. additionOn completion of the addition
  2. stirringstirred overnight
  3. customThe solution was evaporated under reduced pressure to dryness
  4. customThe solid obtained
  5. washwas washed with a solution of sodium acetate
  6. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-eb0648a2166841f8bb65d587ff7953ac
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988695

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