Hydrochloric Acid → 2-Amino-6-(2-iodophenoxymethyl)benzonitrile

HRID 1364473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364473
[Sn](Cl)Cl.Cl.[I:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[O:8][CH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:11]=1[C:12]#[N:13].[OH-].[K+]>>[NH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:10]([CH2:9][O:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[I:5])[C:11]=1[C:12]#[N:13]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 247775372-(2-Iodophenoxymethyl)-6-nitrobenzonitrile

Produkt 1

HCID 247775412-Amino-6-(2-iodophenoxymethyl)benzonitrileAusbeute 34,6 %

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

To a cooled (15° C.) and stirred solution of tin (II) chloride (0.74 g, 3.29 mmol) and con. hydrochloric acid (2.0 mL) was added a solution of 2-(2-iodophenoxymethyl)-6-nitrobenzonitrile (250.0 mg, 0.66 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 3 hours. The reaction mixture was poured on to crushed-ice and potassium hydroxide solution, stirred, extracted with dichloromethane, filtered and dried. Purification by silica gel chromatography (dichloromethane) yielded 80 mg of 2-amino-6-(2-iodophenoxymethyl)benzonitrile.

Aufarbeitung

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. additionThe reaction mixture was poured on
  3. stirringstirred
  4. extractionextracted with dichloromethane
  5. filtrationfiltered
  6. customdried
  7. customPurification by silica gel chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-92a8ffd3946c470ab6326a1cf4ac2142
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888366B2

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