Hydrochloric Acid → HCID 69042340, compound

HRID 494199Notes

Reaction equation

HRID 494199 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.O.[Sn](Cl)Cl.Cl>C(O)C>[NH2:12][C:10]1[CH:9]=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 690434665-Chloro-7-nitroquinoline

Product 1

HCID 69042340HCID 69042340, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-7-nitroquinoline (D82) (50 mg, 0.24 mmol) was treated with tin dichloride dihydrate (216 mg, 0.96 mmol) and conc. hydrochloric acid (2 ml) in ethanol (5 ml) at 70° C. for 4 h. After cooling to room temperature and the ethanol removed in vacuo then the residue was dissolved in water and neutralised with potassium carbonate. This was then extracted with EtOAc which was dried over MgSO4 and concentrated in vacuo to give the title compound as a brown solid (18 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.78 (d, 1H), 8.39 (d, 1H), 7.25 (dd, 1H), 7.18 (d, 1H), 7.11 (d, 1H).

Workup

  1. customthe ethanol removed in vacuo
  2. dissolutionthe residue was dissolved in water and neutralised with potassium carbonate
  3. extractionThis was then extracted with EtOAc which
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92a1262d2eda4d8fad91cdecfba76ee5
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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