Water → HCID 59457670, compound

HRID 1711097Notes

Reaction equation

HRID 1711097 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:10]2[S:11][C:12]([C:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH:15]=3)=[CH:13][C:9]=2C=[CH:7][CH:6]=1.[NH4+:30].[Cl-].O>CCO.[Fe]>[NH2:27][C:25]1[CH:24]=[CH:23][C:3]([O:4][C:5]2[CH:6]=[CH:7][N:30]=[C:9]3[CH:13]=[C:12]([C:14]4[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH:15]=4)[S:11][C:10]=23)=[C:2]([F:1])[CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66649177HCID 66649177, compound

Product 1

HCID 59457670HCID 59457670, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of the nitro compound 390 (358.2 mg, 0.87 mmol) and NH4Cl (39.4 mg, 0.74 mmol) in EtOH (8.7 mL)/water (4.3 mL) at 100° C. Fe powder (411.3 mg, 7.36 mmol) was added in one portion and the mixture was heated to reflux under vigorous stirring for 40 min. It was then filtered through Celite®, the Celite® was washed with EtOH and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in DCM, washed with water, dried (anhydrous Na2SO4) and concentrated under reduced pressure affording 391 (256.5 mg, 77% yield) as a white solid. LCMS:(M+H) 384.2.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationIt was then filtered through Celite®
  4. washthe Celite® was washed with EtOH
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DCM
  7. washwashed with water
  8. dry with materialdried (anhydrous Na2SO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67193c3fecbe4bf5ab76a61adb920597
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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