Sodium Chloride → 5-Nitro-1H-indole-2-carboxylic acid propylamide

HRID 450719

Reaction equation

HRID 450719 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([OH:15])=O)=[CH:7]2)([O-:3])=[O:2].[CH2:16]([NH2:19])[CH2:17][CH3:18].[Cl-].[Na+]>CN(C)C=O.O>[CH2:16]([NH:19][C:13]([C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[O:15])[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 7852PropylamineHCID 3512915-Nitroindole-2-carboxylic acid

Product 1

HCID 670239755-Nitro-1H-indole-2-carboxylic acid propylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-nitro-1H-indole-2-carboxylic acid (6.95 g, 33.7 mmol) in N,N-dimethylformamide (DMF)/pyridine (1/1, 150 ml) N,N′-carbonyl-diimidazole (5.47 g, 33.71 mmol) was added. The mixture was stirred at 80° C. for 1 h. At 0° C. propylamine (9.96 g, 168.56 mmol) was added. The mixture was stirred at 0° C. for 1 h and then at room temperature for 16 h. The solution was diluted with water (2 I). After addition of sodium chloride the product precipitated. After filtration the residue was washed with water and pentane, and dried in a vacuum oven at 50° C. to give the product as a yellow powder.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. waitat room temperature for 16 h
  3. customprecipitated
  4. filtrationAfter filtration the residue
  5. washwas washed with water and pentane
  6. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-1e80d39d99c34aa49004d959ce0d27c2
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Linked notes

Loading…