Ammonium formate → 2-amino-N-(4-methoxy-quinolin-8-yl)benzenesulfonamide

HRID 513805Notes

Reaction equation

HRID 513805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13](Cl)=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[O:22][CH3:23])(=[O:10])=[O:9].C([O-])=O.[NH4+]>CC(O)=O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[O:22][CH3:23])(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 681830532-Amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 681829902-amino-N-(4-methoxy-quinolin-8-yl)benzenesulfonamideYield 32.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

10% Pd—C (97 mg) was added to a solution of 2-amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-benzenesulfonamide 570 (470 mg, 1.8 mmol), ammonium formate (571 mg, 9.2 mmol) in 50% AcOH (10 ml) and the mixture was heated to 70° C. for 15 h. After cooling, the solvent was removed in vacuo. The residue was dissolved in EtOAc (100 ml) and the organic phase was washed with sat. NaHCO3 solution (50 ml), dried (MgSO4) concentrated in vacuo. The crude residue was purified by column chromatography DCM/MeOH (99:1) as the eluent to give the title compound (191 mg, 32%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (100 ml)
  4. washthe organic phase was washed with sat. NaHCO3 solution (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography DCM/MeOH (99:1) as the eluent

Sources & evidence

ORD record
ord-a01f488307ec41a694405a51936e1d49
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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