HCID 69935099, compound → HCID 67168664, compound

HRID 536055Notes

Reaction equation

HRID 536055 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([S:12]([NH:15][CH3:16])(=[O:14])=[O:13])=[C:5]([F:17])[CH:4]=1>CO.[Pd]>[NH2:9][C:8]1[C:3]([N:2]([CH3:1])[CH3:18])=[CH:4][C:5]([F:17])=[C:6]([S:12]([NH:15][CH3:16])(=[O:13])=[O:14])[CH:7]=1

Participants

4

Reactant 1

HCID 69935099HCID 69935099, compound

Product 1

HCID 67168664HCID 67168664, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(dimethylamino)-2-fluoro-N-methyl-5-nitrobenzenesulfonamide (4.0 g, 14.3 mmol) in MeOH (100 mL) was treated with 10% Pd/C (400 mg) and stirred under H2 (50 psi) for 16 hours before being filtered, concentrated, and subjected to flash chromatography (33-50% EtOAc-petroleum ether) to give 5-amino-4-(d imethylamino)-2-fluoro-N-methylbenzenesulfonamide as a white solid (2.5 g, 71%). 1H NMR (400 MHz, CDCl3) δ ppm 7.13 (d, J=7.28 Hz, 1 H), 6.75 (d, J=11.69 Hz, 1 H), 4.58 (q, J=4.85 Hz, 1 H), 3.87 (br. s., 2 H), 2.66 (d, J=5.51 Hz, 3 H). MS (m/z) 248.1 (M+H+).

Workup

  1. filtrationbefore being filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8299bb49a1e34f9395de41fa0513efd7
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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