Formic Acid → 4-(4-Chloro-butoxy)-2-(naphthalene-1-sulfonylmethyl)-phenyl amine

HRID 2240043Notes

Reaction equation

HRID 2240043 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N+:27]([O-])=O)=[C:11]([CH2:13][S:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:12]=1.C(O)=O>C1COCC1.CO.[Pd]>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:27])=[C:11]([CH2:13][S:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:12]=1

Participants

6

Reactant 2

HCID 284Formic AcidHCID 686789021-[5-(4-Chloro-butoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene

Product 1

HCID 686794554-(4-Chloro-butoxy)-2-(naphthalene-1-sulfonylmethyl)-phenyl amineYield 84.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[5-(4-chloro-butoxy)-2-nitro-phenyl-methanesulfonyl]-naphthalene (1.94 g, 4.5 mmoles) and 10% Pd/C in THF (20 mL), methanol (20 mL), and formic acid (5 mL) was hydrogenated in a Parr hydrogenation bottle (250 mL) at 40 lb/in2 for 20 hours. The mixture was filtered through Celite, and the filtrate was diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated under vacuum. The crude product was purified by flash chromatography using as eluent 5% EtOAc/CH2Cl2 to afford the title compound as an off-white solid (1.54 g, 3.8 mmoles).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-375bc30268a64b20b6a37d0af190b9f4
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

Loading…