Potassium Nitrate → 4-Bromo-5-nitroisoquinoline

HRID 895673

Reaktionsgleichung

Reaktionsgleichung von HRID 895673
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9][CH:8]=1.COC1C(OCOC)=C(B2OC(C)(C)C(C)(C)O2)C=CC=1OC>S(=O)(=O)(O)O>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N+:1]([O-:4])=[O:2])[CH:10]=[N:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 24434Potassium NitrateHCID 737434-BromoisoquinolineHCID 223807722-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

Produkt 1

HCID 2712804-Bromo-5-nitroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Potassium nitrate (5.34 g; 0.052 mol) was added to 20 ml of concentrated sulfuric acid and slowly dissolved by careful heating. The resulting solution was added dropwise to a solution of 4-bromoisoquinoline (10 g; 0.048 mol) dissolved in 40 ml of the same acid at 0° C. After removal of the cooling bath, the solution was stirred for one hour at room temperature. The reaction mixture was then poured onto crushed ice (400 g) and made basic with ammonium hydroxide. The resulting yellow precipitate was collected by filtration and the filtrate was extracted with diethyl ether (3×500 ml), dried (Na2SO4), and concentrated to give a yellow solid that was combined with the initial precipitate. Recrystallization from methanol gave 12.1 g (89%) of slightly yellow crystals: mp 172-174° C.; 1H NMR: (300 MHz, CDCl3): 9.27 (s, 1H); 8.87 (s, 1H); 8.21 (dd, 1H, J=6.6, 1.2 Hz); 7.96 (dd, 1H, J=6.6, 1.2 Hz); 7.73 (t, 1H, J=7.5 Hz). CIMS m/z: 253 (M+H+, 100%); 255 (M+H++2, 100%). Anal. Calc'd for C9H5BrN2O2: C, 42.72; H, 1.99; N, 11.07. Found: C, 42.59; H, 1.76; N, 10.87.

Aufarbeitung

  1. dissolutionslowly dissolved by careful heating
  2. customAfter removal of the cooling bath
  3. additionThe reaction mixture was then poured
  4. customonto crushed ice (400 g)
  5. filtrationThe resulting yellow precipitate was collected by filtration
  6. extractionthe filtrate was extracted with diethyl ether (3×500 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give a yellow solid
  10. customRecrystallization from methanol
  11. customgave 12.1 g (89%) of slightly yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-e085fb8b699049ba854c3f8b8b913c33
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916832B2

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