Ammonium Chloride → HCID 66649280, compound

HRID 418709Notes

Reaction equation

HRID 418709 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:17]2[S:25][C:24]3[C:19](=[N:20][CH:21]=[CH:22][C:23]=3[O:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][C:28]=3[F:36])[CH:18]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][Cl:16].[NH4+].[Cl-]>CO.O.C(OCC)(=O)C.[Fe]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:17]2[S:25][C:24]3[C:19](=[N:20][CH:21]=[CH:22][C:23]=3[O:26][C:27]3[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][C:28]=3[F:36])[CH:18]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][Cl:16]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 66649121HCID 66649121, compound

Product 1

HCID 66649280HCID 66649280, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of nitro compound 333 (32 mg, 0.57 mmol) in a mixture of MeOH (2 mL) and water (1 mL) were added iron powder (16 mg, 0.29 mmol) and NH4Cl (2.8 mg, 0.05 mmol). The reaction mixture was heated to reflux for 2.5 hrs, cooled to room temperature, diluted with ethyl acetate, filtered, and rinsed with AcOEt. The filtrate was successively washed with sat. ammonium chloride, sat. NaHCO3, water, dried over anhydrous MgSO4, filtered, and concentrated to afford title compound 334 (25 mg, 83% yield) as a pale yellow solid. MS (m/z): 521.0 and 523.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2.5 hrs
  3. filtrationfiltered
  4. washrinsed with AcOEt
  5. washThe filtrate was successively washed with sat. ammonium chloride, sat. NaHCO3, water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8e9206db181a43e494701780e215f2c2
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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