Hydrochloric Acid → 2-Amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:21]([O-])=O)[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[H][H]>O1CCOCC1.[C].[Pd]>[ClH:1].[NH2:21][C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:19]=[CH:18][C:17]=1[OH:20]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
4-[3-(4-Chlorophenylsulfonyl)propyl]-2-nitrophenol (10.00 g, 28.11 mmol) was dissolved in 1,4-dioxane (100 ml), 4 N hydrochloric acid solution in 1,4-dioxane (8.43 ml, 33.73 mmol) and 10% palladium-carbon (1.0 g) were added, and the mixture was stirred for 4 hours in an atmosphere of hydrogen gas under 1 atmospheric pressure. The crystals precipitated in the reaction solution were dissolved by adding methanol, the reaction mixture was filtered, and then the resulting filtrate was concentrated under reduced pressure. By crystallizing the resulting residue from acetonitrile-ether, 2-amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochloride (9.71 g, 95%) was obtained.
Workup
- customThe crystals precipitated in the reaction solution
- dissolutionwere dissolved
- additionby adding methanol
- filtrationthe reaction mixture was filtered
- concentrationthe resulting filtrate was concentrated under reduced pressure
- customBy crystallizing the resulting residue from acetonitrile-ether
Sources & evidence
- ORD record
- ord-7dce7a6038b54962bb0b11c56d208334
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05981559
Reaction notes
Loading…