Sulfuric Acid → Methyl 5-bromoisoquinoline-4-carboxylate

HRID 1470482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470482
OS(O)(=O)=O.[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=1.C1C(=O)N([Br:27])C(=O)C1>>[Br:27][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=[CH:6]2

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 11830161Methyl Isoquinoline-4-carboxylate

Produkt 1

HCID 68281832Methyl 5-bromoisoquinoline-4-carboxylateAusbeute 90,2 %

Versuchsvorschrift

To a mixture of conc. H2SO4 (16 mL) and methyl isoquinoline-4-carboxylate (Intermediate-15) (2.8 g, 15 mmol) at 0° C. was added, NBS (3.3 g, 18.7 mmol) slowly and the reaction mixture was allowed to come to RT and stirred overnight. After completion (TLC), it was quenched with ice, neutralized (NaHCO3) and extracted with EtOAc (50 mL×3). The organic phase was separated, dried (Na2SO4) and concentrated to give dark brown oil (3.6 g) as crude product that was purified by flash column chromatography (25% EtOAc in Hexanes) to furnish the desired compound (1.4 g, 35%).

Aufarbeitung

  1. additionwas added
  2. customto come to RT
  3. customAfter completion (TLC), it was quenched with ice
  4. extractionextracted with EtOAc (50 mL×3)
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f895bbcf45840f2a5ec6561f168bb49
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006442B2

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