Ammonium Chloride → HCID 58236601, compound

HRID 409970Notes

Reaction equation

HRID 409970 reaction equation
[C:1]([O:5][C:6](=[O:42])[N:7]([CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22]2[S:30][C:29]3[C:24](=[N:25][CH:26]=[CH:27][C:28]=3[O:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][C:33]=3[F:41])[CH:23]=2)=[CH:20][CH:21]=1)[CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.O.[Fe]>[C:1]([O:5][C:6](=[O:42])[N:7]([CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22]2[S:30][C:29]3[C:24](=[N:25][CH:26]=[CH:27][C:28]=3[O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][C:33]=3[F:41])[CH:23]=2)=[CH:20][CH:21]=1)[CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])([CH3:4])([CH3:2])[CH3:3]

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-7fab9551c396455ea4d2f95523deb7a7
Source dataset
uspto-grants-2014_06
Patent number
US08759522B2

Reaction notes

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