Bromine → Methyl 2-amino-5-bromonicotinate

HRID 1690326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690326
[Br:1]Br.[NH2:3][C:4]1[N:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>CC(O)=O>[NH2:3][C:4]1[N:13]=[CH:12][C:11]([Br:1])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 351633Methyl 2-aminopyridine-3-carboxylate

Produkt 1

HCID 2763453Methyl 2-amino-5-bromonicotinateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Bromine (0.7 mL, 14 mmole) was added dropwise to a stirred solution of methyl 2-aminonicotinate (2.0 g, 13 mmole) in HOAc (50 mL). A suspension formed within 30 min. The reaction was allowed to stir at room temperature for 2 h, then was concentrated under vacuum. The residue was triturated with 1.0 N Na2CO3 (50 mL) and the solid was collected by suction filtration. The solid was washed with H2O (50 mL) and dried under vacuum to give the title compound (2.95 g, 98%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=2.5 Hz, 1 H), 8.23 (d, J=2.5 Hz, 1 H), 6.40 (br s, 2 H), 3.90 (s, 3 H).

Aufarbeitung

  1. customA suspension formed within 30 min
  2. concentrationwas concentrated under vacuum
  3. customThe residue was triturated with 1.0 N Na2CO3 (50 mL)
  4. filtrationthe solid was collected by suction filtration
  5. washThe solid was washed with H2O (50 mL)
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d28985f22d5040fa9b6a0f9516a17d0d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153652B2

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