Hydrazine hydrate (1:1) → 2-(2-Chloro-ethoxy)-4-fluoro-6-(naphthalene-1-sulfonyl-methyl)-phenylamine

HRID 2240057Notes

Reaction equation

HRID 2240057 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([N+:26]([O-])=O)=[C:7]([CH2:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:8]=[C:9]([F:11])[CH:10]=1.O.NN>C(O)C.[Pd]>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([CH2:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[C:6]=1[NH2:26]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598428001-[3-(2-Chloroethoxy)-5-fluoro-2-nitrophenylmethanesulfonyl]-naphthalene

Product 1

HCID 686788602-(2-Chloro-ethoxy)-4-fluoro-6-(naphthalene-1-sulfonyl-methyl)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[3-(2-chloro-ethoxy)-5-fluoro-2-nitro-phenylmethanesulfonyl]-naphthalene (1.0 g, 2.36 mmoles) in ethanol (25 mL) was stirred under nitrogen in a round bottom flask at 60° C. 10% Pd/C was added, and the temperature was increased to 80° C. Hydrazine hydrate (2.0 mL) was added dropwise and the mixture was stirred at reflux for 3 hours. Reaction mixture was filtered off through Celite, and the solution was washed with H2O (3×), dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.91 g, 2.31 mmoles).

Workup

  1. temperaturethe temperature was increased to 80° C
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 3 hours
  4. customReaction mixture
  5. filtrationwas filtered off through Celite
  6. washthe solution was washed with H2O (3×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7301d20f2b7a4f29a61589c1affd32fb
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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