Hydrochloric Acid → N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

HRID 2423335Notes

Reaction equation

HRID 2423335 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([F:14])[CH:4]=1)#[N:2].[ClH:15]>CO.CCOCC.[Pd]>[ClH:15].[F:14][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:1][NH2:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15981202N-(4-Cyano-2-fluorophenyl)methanesulfonamide

Product 1

HCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-cyano-2-fluoro-1-methanesulfonylaminobenzene (1.03 g) prepared in step 2 was dissolved in methanol (20 mL) and added a catalytic amount of 10 wt. % Pd/C and concentrated HCl (3 mL) to hydrogenate. The reaction solution was stirred at room temperature for 1 hour. The resulting solution was diluted with ether, filtered through celite, concentrated under reduced pressure and washed with ethylacetate to yield the title compound (1.13 g, 92%).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated under reduced pressure
  3. washwashed with ethylacetate

Sources & evidence

ORD record
ord-ee4a7aee47aa427e9532bd2dd841e0d5
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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