Sulfuric Acid → 2-Bromo-12H-chromeno[2,3-b]quinolin-12-one

HRID 717682Notes

Reaction equation

HRID 717682 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:6]([CH:19]=O)[C:5]2=[O:21].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]1=[N:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH:19]=[C:6]1[C:5]2=[O:21]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 866606206-Bromo-4-oxo-2-(phenylamino)-4H-chromene-3-carbaldehyde

Product 1

HCID 666150262-Bromo-12H-chromeno[2,3-b]quinolin-12-oneYield 77%

Procedure

To the product of Step A (1 g; 2.92 mmol) concentrated H2SO4 (1 ml) was gently added with stirring. The mixture was kept in sealed vial for 24 h, at room temperature, than poured onto ice water and extracted with CH2Cl2 (50 ml). The organic layer was washed with NaHCO3 solution, H2O, dried over MgSO4 and filtered. The filtrate was distilled off and the residue was crystallized from CH3CN to give the title compound (0.73 g, 77%), as green yellow solid. 1H-NMR (CDCl3) 9.28 (s, 1H); 8.44 (d, 1H, J=2.1 Hz); 8.1-8.06 (m, 2H); 7.94-7.84 (m, 2H); 7.63 (t, 1H, J=7.88 Hz); 7.51 (d, 1H, J=8.83 Hz).

Workup

  1. customsealed vial for 24 h
  2. additionat room temperature, than poured onto ice water
  3. extractionextracted with CH2Cl2 (50 ml)
  4. washThe organic layer was washed with NaHCO3 solution, H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. distillationThe filtrate was distilled off
  8. customthe residue was crystallized from CH3CN

Sources & evidence

ORD record
ord-c1b6e19884c64fccad3d83b5d57bbfda
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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