HCID 11562119, compound → HCID 11590559, compound

HRID 735255Notes

Reaction equation

HRID 735255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[NH:8][C:7](=[O:13])[C:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([N+:23]([O-])=O)[CH:16]=1)([CH3:14])[C:5]2=[O:26]>C(O)(=O)C>[NH2:23][C:17]1[CH:16]=[C:15]([C:6]2([CH3:14])[C:5](=[O:26])[C:4]3[C:9](=[C:10]([Br:12])[CH:11]=[C:2]([Br:1])[CH:3]=3)[NH:8][C:7]2=[O:13])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

3

Reactant 1

HCID 11562119HCID 11562119, compound

Product 1

HCID 11590559HCID 11590559, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6,8-dibromo-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.14 g, 0.29 mmol) in acetic acid (5.0 mL) was treated with SnCl2-2H2O (0.26 g, 1.16 mmol) for 4 hours at room temperature. After the reaction was completed, yellow residue was obtained by evaporating solvent under reduced pressure. The residue was diluted with 1N HCl solution (200 mL), and was extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with brine (200 mL×2) and water (200 mL×2) and dried over anhydrous MgSO4. After evaporation of the solvent, the pure objective compound (56 mg, 42%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=2:1): 1H NMR (200 MHz, CDCl3) δ 1.73 (s, 3H, CH3), 3.77 (s, 3H, OCH3), 4.11 (br s, 2H, NH2), 6.44-6.58 (m, 2H, ArH), 6.65 (d, J=8.6 Hz, 1H, ArH), 7.77 (d, J=2.2 Hz, 1H, ArH) ; HRMS m/e cacld. for C17H14N2O3Br2 451.9371, found 451.9385.

Workup

  1. customyellow residue was obtained
  2. customby evaporating solvent under reduced pressure
  3. additionThe residue was diluted with 1N HCl solution (200 mL)
  4. extractionwas extracted with ethyl acetate (200 mL×3)
  5. washThe combined organic layer was washed with brine (200 mL×2) and water (200 mL×2)
  6. dry with materialdried over anhydrous MgSO4
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-d3fe28c48e7b4658ae49dad5ffa92965
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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