Ammonium Chloride → HCID 58236601, compound

HRID 1026813Notes

Reaction equation

HRID 1026813 reaction equation
[F:1][C:2]1[CH:39]=[C:38]([N+:40]([O-])=O)[CH:37]=[CH:36][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:40][C:38]1[CH:37]=[CH:36][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:39]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58236620HCID 58236620, compound

Product 1

HCID 58236601HCID 58236601, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To nitro compound 328 (0.20 g, 0.33 mmol) in MeOH (75 mL) was added iron dust (0.37 g, 6.7 mmol) and ammonium chloride (0.089 g, 1.7 mmol) in water (5 mL). The resulting mixture was heated to reflux for 4 h, then cooled, filtered through celite and concentrated. The residue was partitioned between ethyl acetate and water, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The product 329 (0.18 g, 95%) was used crude in the next step. LRMS (M+H): 569.5

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. customThe residue was partitioned between ethyl acetate and water
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-586f82936dd549a093a9a20a3d0ae152
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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