Potassium Nitrate → 4-Bromo-5-nitroisoquinoline

HRID 2227363

反応式

HRID 2227363 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 2712804-Bromo-5-nitroisoquinoline

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

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, 1 H, J=6.6, 1.2 Hz); 7.73 (t, 1 H, 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.

後処理

  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

出典と根拠

ORDレコード
ord-2ab7714909f94148b61f9f08b0c924e7
出典データセット
uspto-grants-2002_07
特許番号
US06413977B1

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