Ammonium Chloride → HCID 59426340, compound

HRID 502293Notes

Reaction equation

HRID 502293 reaction equation
[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=3)[CH:7]=[C:6]2[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>[Fe].CCO.O>[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=3)[CH:7]=[C:6]2[C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59425808HCID 59425808, compound

Product 1

HCID 59426340HCID 59426340, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-cyclobutyl-6-methoxy-2-(4-nitro-phenyl)-1H-indole (0.83 g, 2.60 mmol), iron powder (0.84 mg, 15.0 mmol), ammonium chloride (0.96 g, 18.0 mmol), and EtOH/water (25 mL/8 mL) was stirred at 80° C. for 1 h and concentrated. The residue was suspended in DMF (20 mL) and MeOH/CH2Cl2 (1:1, 20 mL). The mixture was passed through a Celite pad, washed with MeOH/CH2Cl2 (1:1), concentrated and water was added to afford a precipitate which was collected by filtration and washed with water. The solid was dissolved in CH2Cl2, dried over MgSO4, concentrated and purified on silica gel (EtOAc/hexane 20%) to provide 4-(1-cyclobutyl-6-methoxy-1H-indole-2-yl)-phenylamine (0.57 mg, 75%) as a white solid.

Workup

  1. concentrationconcentrated
  2. washwashed with MeOH/CH2Cl2 (1:1)
  3. concentrationconcentrated
  4. additionwater was added
  5. customto afford a precipitate which
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. dissolutionThe solid was dissolved in CH2Cl2
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. custompurified on silica gel (EtOAc/hexane 20%)

Sources & evidence

ORD record
ord-4785e4b7c2af402db4da0f322ac894ea
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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