Ammonium Chloride → HCID 68474590, compound

HRID 1466488Notes

Reaction equation

HRID 1466488 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[NH:7][C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[CH:5]2.[NH4+].[Cl-]>O1CCCC1.CO.O.[Fe]>[NH2:11][C:9]1[CH:10]=[C:2]([CH3:1])[CH:3]=[C:4]2[C:8]=1[NH:7][C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[CH:5]2

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 68476582HCID 68476582, compound

Product 1

HCID 68474590HCID 68474590, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5-Methyl-7-nitro-2-(pyridin-2-yl)-1H-indole (6.9 g, 27.3 mmol) prepared in Preparation 8 was dissolved in a solvent mixture of tetrahydrofuran (130 mL), methanol (1 mL) and water (130 mL), and NH4Cl (14.6 g, 27.3 mmol) was added thereto. The reaction mixture was warmed to 60° C., iron powder (15.2 g, 273 mmol) was added thereto, and the mixture was stirred for 30 min. After completion of the reaction, the reaction mixture was filtered through a cellite to remove the solid. Certain amount of the solvent was removed under reduced pressure from the resulting solution, which was then extracted with EtOAc. The extracted organic material was dried over MgSO4, and the solvent was removed under reduced pressure to give the title compound (5.0 g, Yield 40%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through a cellite
  4. customto remove the solid
  5. customCertain amount of the solvent was removed under reduced pressure from the resulting solution, which
  6. extractionwas then extracted with EtOAc
  7. dry with materialThe extracted organic material was dried over MgSO4
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b863849fdf854ce3a40b8d5340080d7c
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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