Ammonium Chloride → HCID 18367942, compound

HRID 379836Notes

Reaction equation

HRID 379836 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)(=[O:3])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 18367931HCID 18367931, compound

Product 1

HCID 18367942HCID 18367942, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-acetylamino-6-chloro-2-(3-nitrobenzoyl)indole (step 3, 2.68 g, 7.5 mmol), iron powder (1.7 g, 30 mmol) and ammonium chloride (0.8 g, 17 mmol) in 70% aqueous ethanol (70 ml) was heated at reflux for 1 h, and then cooled and filtered through a pad of Celite. The filtrate was concentrated and the residue partitioned between water (50 ml) and ethyl acetate (150 ml). The organic layer was separated, dried (MgSO4) and slovent removed by evaporation to afford 2.6 g (quant.) of the title compound as yellow amorphous solids. 1H-NMR (CDCl3) δ: 9.83 (1H, br s), 8.63 (1H, brs), 8.16 (1H, d, J=8.8 Hz), 7.35-7.21 (2H, m), 7.15-6.98 (3H, m), 6.88 (1H, dd, J=8.8, 1.8 Hz), 2.25 (3H, s) The signal due to NH2 was not observed.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue partitioned between water (50 ml) and ethyl acetate (150 ml)
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. customslovent removed by evaporation

Sources & evidence

ORD record
ord-ab1f0dada4d243c3bbd725f39926ddec
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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