2-Nitro-p-toluenesulphonyl chloride → 2-Nitrobenzenesulfonamide

HRID 2358950Notes

Reaction equation

HRID 2358950 reaction equation
COC1C=C2C(=C(N)C=1)[N:9]=C(C)C=C2.C[C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[C:18]([N+:26]([O-:28])=[O:27])[CH:17]=1>N1C=CC=CC=1>[N+:26]([C:18]1[CH:17]=[CH:16][CH:21]=[CH:20][C:19]=1[S:22]([NH2:9])(=[O:24])=[O:23])([O-:28])=[O:27]

Participants

4

Reactant 2

HCID 1046892-Nitro-p-toluenesulphonyl chlorideHCID 124995536-Methoxy-2-methyl-8-quinolinamine

Product 1

HCID 1385102-NitrobenzenesulfonamideYield 153.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-methoxy-2-methylquinolin-8-amine 2a (0.19 g, 1.0 mmol) in pyridine (5 ml) was added 4-methyl-2-nitrobenzenesulfonyl chloride (0.24 g, 1.0 mmol). The mixture was stirred at room temperature overnight and precipitated with H2O. The crude product was filtered and recrystallized from EtOH to afford nitrobenzenesulfonamide (0.31 g, 79%) as red crystal. 1H NMR (300 MHz, CDCl3) δ 10.1 (br, 1H); 8.04 (d, 1H), 7.86 (d, 1H), 7.62 (m, 2H), 7.39 (d, 1H), 7.24 (d, 1H), 6.73 (s, 1H), 3.88 (s, 3H), 2.66 (s, 3H), 2.41 (s, 3H); ESI-MS (M++1): 388.0. To a suspension of above nitro compound (0.20 g, 0.56 mmol) in EtOH (5 ml) was added SnCl2 (0.32 g, 1.7 mmol) slowly. The mixture was refluxed for 2 h. After removal of EtOH, the residue was treated with 1M NaOH. The aqueous solution was extracted with CH2Cl2. The combined organic phases were washed by brine, dried over Na2SO4, and concentrated to yield 9a (0.18 g, 92%) as white solid. 1H NMR (300 MHz, CDCl3) δ 9.42 (br, 1H); 7.83 (d, 1H), 7.65 (d, 1H), 7.30 (s, 1H), 7.23 (d, 1H), 6.64 (s, 1H), 6.48 (d, 1H), 6.42 (s, 1H), 3.80 (s, 3H), 2.61 (s, 3H), 2.17 (s, 3H); ESI-MS (M++1): 358.1.

Workup

  1. customprecipitated with H2O
  2. filtrationThe crude product was filtered
  3. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-66425b4b38704a36baa60ee492056b7a
Source dataset
uspto-grants-2014_04
Patent number
US08685963B2

Reaction notes

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