Ammonium Chloride → HCID 15870194, compound

HRID 365604Notes

Reaction equation

HRID 365604 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:24]([O-])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:23])[C:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:23])[C:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[NH2:24]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 15870193HCID 15870193, compound

Product 1

HCID 15870194HCID 15870194, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-Chloro-4-{5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene (14.38 g, 39.0 mmol) [prepared as in Example 4, Step (c)] was dissolved in ethanol (300 ml) and an aqueous solution of ammonium chloride (14.0 g in 150 ml) and iron powder (14.0 g) were added to the solution. The reaction mixture was refluxed for 30 min, then cooled to room temperature and filtered. The filtrate was concentrated, diluted with water, and extracted with ether and methylene chloride. The organic layer were combined, washed with brine and dried over sodium sulfate. Evaporation gave 3-chloro-4-{5-(4-methylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}aniline (12.09 g, 92%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with water
  5. extractionextracted with ether and methylene chloride
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customEvaporation

Sources & evidence

ORD record
ord-0d1ecd1e8861402bad0fd643e221db33
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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