Ammonium Chloride → 3-(4-Nitrophenyl)-1H-indole-2-carboxamide

HRID 230544Notes

Reaction equation

HRID 230544 reaction equation
[Cl-].[NH4+:2].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([O:23]CC)=O)=[CH:8][CH:7]=1)([O-:5])=[O:4]>N>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([NH2:2])=[O:23])=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 12404967ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylate

Product 1

HCID 577628413-(4-Nitrophenyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Conditions

Temperature
125 °C

Procedure

A solution of 0.5 g of ammonium chloride in 30 ml of concentrated aqueous ammonia is added to a solution of 3.3 g of ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylate in 50 ml of 7N methanolic ammonia. The solution is then heated in a sealed tube at 125° C. for 15 hours. After cooling, the solid formed is filtered off, washed with water, and then filter-dried. After drying under vacuum, 1.5 g of 3-(4-nitrophenyl)-1H-indole-2-carboxamide are obtained, the characteristics of which are as follows:

Workup

  1. temperatureAfter cooling
  2. customthe solid formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customfilter-dried
  6. dry with materialAfter drying under vacuum, 1.5 g of 3-(4-nitrophenyl)-1H-indole-2-carboxamide
  7. customare obtained

Sources & evidence

ORD record
ord-2e700df9130f4fd5b2bcab143a87adda
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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