Dimethylformamide → 2-Amino-4-methoxy-3-methylbenzonitrile

HRID 402201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402201
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:9]([O-:12])([O-])=O.[K+].[K+].CI.[CH3:17][N:18](C=O)C>O>[NH2:8][C:1]1[C:6]([CH3:7])=[C:5]([O:12][CH3:9])[CH:4]=[CH:3][C:2]=1[C:17]#[N:18]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12878168Hept-6-en-1-amine

Produkt 1

HCID 552964222-Amino-4-methoxy-3-methylbenzonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of compound 76 (12 g, 0.08 mol), K2CO3 (11 g, 0.08 mol) in dry DMF (200 mL) was stirred for 15 min at RT. To this was added MeI (13.6 g, 0.096 mol) and the mixture was stirred for 4 h at RT. The reaction mixture was diluted with water (800 mL), extracted with 30% ethyl acetate in pet. ether (3×300 mL). The combined organic layers were washed with water and brine, dried and concentrated to give a crude product. The crude product was washed with pet. ether to give pure title compound (12 g, 93%).

Aufarbeitung

  1. stirringthe mixture was stirred for 4 h at RT
  2. extractionextracted with 30% ethyl acetate in pet. ether (3×300 mL)
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude product
  7. washThe crude product was washed with pet. ether

Quellen und Nachweise

ORD-Eintrag
ord-1f3864484206448f97d086553f954f1f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741926B2

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