3-(Benzenesulfonyl)-8-nitroquinoline → 3-(Phenylsulfonyl)-8-quinolinamine

HRID 2092187Notes

Reaction equation

HRID 2092187 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][C:10]([S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[CH:9]2)([O-])=O>C(O)(=O)C.[Fe]>[C:17]1([S:14]([C:10]2[CH:11]=[N:12][C:13]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[CH:5][C:4]=3[NH2:1])(=[O:15])=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 534255033-(Benzenesulfonyl)-8-nitroquinoline

Product 1

HCID 534255023-(Phenylsulfonyl)-8-quinolinamineYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 8-nitro-3-(phenylsulfonyl)quinoline (3.70 g, 11.77 mmol) in acetic acid (40 ml) at 80° C. was added iron powder (3.29 g, 58.86 mmol) in portions over 5 mins. The resulting suspension was stirred for a further 30 mins. It was then cooled down to room temperature and filtered. The solid was washed with acetic acid and the collected filtrates concentrated. The residue was dissolved in CH2Cl2 and washed with ammonium hydroxide solution (25%), water and then dried over MgSO4. The organic layer was filtered and then evaporated to afford the title compound (3.20 g, 96%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with acetic acid
  3. concentrationthe collected filtrates concentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with ammonium hydroxide solution (25%), water
  6. dry with materialdried over MgSO4
  7. filtrationThe organic layer was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-ce8d240f55d848ad93871c728629f545
Source dataset
uspto-grants-2013_05
Patent number
US08440694B2

Reaction notes

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