N-bromobutanimide → Methyl 2-amino-5-bromoisonicotinate

HRID 420519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420519
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1.C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:9]([Br:19])=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Produkt 1

HCID 25307230Methyl 2-amino-5-bromoisonicotinateAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-18 °C

Versuchsvorschrift

A solution of 2-amino-isonicotinic acid methyl ester (5.58 g, 36.7 mmol) in DMF (56 mL) was cooled to −18° C. (ice/MeOH bath), treated with NBS (7.21 g, 38.5 mmol), and stirred at −18° C. for 1 h. The reaction mixture was diluted in AcOEt (500 mL) and washed with water (2×250 mL). The organic layer was dried over Na2SO4, filtered and evaporated to yield the crude title compound (3.0 g, 13.0 mmol, 35%) as a yellow solid, which was used in the next step without further purification. MS: 231 [M+1]+; HPLC: AtRet=0.70.

Aufarbeitung

  1. washwashed with water (2×250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e9ee3d3716b4441ea531b3b4e400860c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097617B2

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