Ammonium Chloride → HCID 18005184, compound

HRID 1603774Notes

Reaction equation

HRID 1603774 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2)([O-])=O.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18005131HCID 18005131, compound

Product 1

HCID 18005184HCID 18005184, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of nitroindole (D46) (0.63 g, 2.5 mmol), and iron powder (0.41 g, 7.2 mmol) in methanol (20 ml) was added a solution of ammonium chloride (0.66 g, 12.4 mmol) in water (13 ml). The mixture was then heated under reflux for 12 h, then filtered while hot and evaporated. The residue was diluted with water and extracted with dichloromethane. The organic extract was washed with brine, dried and evaporated to give the title compound (0.40 g, 72%) as a gum.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 12 h
  3. filtrationfiltered while hot and
  4. customevaporated
  5. additionThe residue was diluted with water
  6. extractionextracted with dichloromethane
  7. extractionThe organic extract
  8. washwas washed with brine
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-576d217d46a74b9b9d7a35f869c1234a
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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