tert-Butanol → 2-Chloro-6-methyl-isonicotinic acid tert-butyl ester

HRID 1432110

Reaktionsgleichung

Reaktionsgleichung von HRID 1432110
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:16][C:17](O)([CH3:19])[CH3:18].CCN(CC)CC>C1(C)C=CC=CC=1.CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([CH3:11])[N:10]=[C:2]([Cl:1])[CH:3]=1)([CH3:19])([CH3:18])[CH3:16]

Komponenten

9

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Produkt 1

HCID 860403662-Chloro-6-methyl-isonicotinic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 0.2 g (1.17 mmol) 2-chloro-6-methyl-isonicotinic acid in 5 ml toluene is treated with 2 drops of DMF and 0.17 ml (2.33 mmol) SOCl2 and refluxed for 4 h. The mixture is concentrated under reduced pressure and the residue is taken up in 1.5 ml DCM, 0.22 ml tBuOH and 0.24 ml Et3N and stirred in the presence of 7 mg (0.06 mmol) DMAP for 18 h. The mixture is diluted with DCM, washed with 10% aqueous citric acid, water and 10% aqueous NaHCO3, dried with sodium sulfate and evaporated. Chromatography of the product on silica gel (hexane/EtOAc 4:1 and 3:1) yields the title compound as a yellowish solid.

Aufarbeitung

  1. temperaturerefluxed for 4 h
  2. concentrationThe mixture is concentrated under reduced pressure
  3. washwashed with 10% aqueous citric acid, water and 10% aqueous NaHCO3
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9ba1d4a1dfe54c9fb5fdb2cba72fd393
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612055B2

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