Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

HRID 542751

Reaktionsgleichung

Reaktionsgleichung von HRID 542751
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].S(=O)(=O)(O)[OH:11].[C:15]1([CH3:21])[CH:20]=CC=C[CH:16]=1.N>CC(O)(C)C.O>[CH3:16][C:15]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:11])([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 1140TolueneHCID 8199283-Methylpyridine-2-carbonitrile

Produkt 1

HCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-cyano-3-methyl pyridine (400 g) is suspended in t-BuOH (800 mL) and the mixture heated to 70° C. Concentrated sulphuric acid (400 mL) is added dropwise over 45 minutes. The reaction is complete after a further 30 minutes at 75° C. The mixture is then diluted with water (400 mL), charged with toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature is kept at 50°-55° C. during the work up. The toluene phase is separated, the aqueous layer reextracted and the combined toluene phases are washed with water. Removal of the toluene yields an oil, N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide, from which solid product may crystallize. Product yield of 97% is determined by internal standard assay on gas chromatograph.

Aufarbeitung

  1. customis kept at 50°-55° C. during the work
  2. customThe toluene phase is separated
  3. washthe combined toluene phases are washed with water
  4. customRemoval of the toluene

Quellen und Nachweise

ORD-Eintrag
ord-becfb2b95d864db7b15047cc42b826f9
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659716

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