Dimethylformamide → Methyl 2-methyl-3-nitrobenzoate

HRID 11747

Reaktionsgleichung

Reaktionsgleichung von HRID 11747
CN([CH:4]=[O:5])C.[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10].IC>O>[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:5][CH3:4])=[O:10]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 160962-Methyl-3-nitrobenzoic acid

Produkt 1

HCID 601165Methyl 2-methyl-3-nitrobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

With reference to FIG. 4, DMF (130 mL) was added to a well mixed 2-methyl-3-nitrobenzoic acid 2 (50 g, 0.28 mol) and KHCO3 (84 g, 0.84 mol) solution. Since the mixture became highly viscous, it was heated to 40° C. with manual shaking. Iodomethane (79 g, 0.56 mol) was added via syringe after the gas evolution had ceased. The resulting orange colored solution was stirred for 12 hours at room temperature. The reaction mixture was poured into water (800 mL), and the resulting precipitate collected by filtration and dried over P2O5 to give pure methyl 2-methyl-3-nitrobenzoate 3 (56 g, 100%) as a white solid: mp. 64.2–65.5° C.; 1H-NMR (CDCl3) δ 8.00 (d, J=7.8 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.39 (t, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.63 (s, 3H); IR (KBr, cm−1) 1724, 1548, 1279; MS (EI): 195 (M+).

Aufarbeitung

  1. filtrationthe resulting precipitate collected by filtration
  2. dry with materialdried over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-137b808493674b5286db3185603fd708
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098307B2

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