Ammonium Chloride → 3-Amino-6-chloro-2-(pyridine-2-carbonyl)indole

HRID 379824Notes

Reaction equation

HRID 379824 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N+:19]([O-])=O)=[C:7]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:19][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 183678596-Chloro-3-nitro-2-(pyridine-2-carbonyl)indole

Product 1

HCID 183678643-Amino-6-chloro-2-(pyridine-2-carbonyl)indole

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-chloro-3-nitro-2-(pyridine-2-carbonyl)indole (step 3, 92 mg, 0.30 mmol), ammonium chloride (8 mg, 0.15 mmol) and iron powder (89 mg, 1.52 mmol) in 70% aqueous ethanol (6 ml) was heated at reflux for 2 h, and then cooled and filtered through a pad of Celite. The pad was washed copiously with a mixture of ethanol/ethyl acetate (1:1 v/v) and the combined washing evaporated. The residue was diluted with ethyl acetate (50 ml), washed with saturated aqueous sodim bicarbonate (30 ml) and dried (Na2SO4). Removal of solvent gave product as crystals.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. filtrationfiltered through a pad of Celite
  5. washThe pad was washed copiously with a mixture of ethanol/ethyl acetate (1:1 v/v)
  6. washthe combined washing
  7. customevaporated
  8. additionThe residue was diluted with ethyl acetate (50 ml)
  9. washwashed with saturated aqueous sodim bicarbonate (30 ml)
  10. dry with materialdried (Na2SO4)
  11. customRemoval of solvent
  12. customgave product as crystals

Sources & evidence

ORD record
ord-88f602edfd8945f99b339cefd338a70a
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…