Hydrochloric Acid → 5-nitro-N-phenyl-1H-indole-2-carboxamide

HRID 1824989Notes

Reaction equation

HRID 1824989 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].CN(C)CCCN=C=NCC.Cl.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C1C=CN=CC=1.ClCCl.CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:15])=[CH:7]2)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3512915-Nitroindole-2-carboxylic acid

Product 1

HCID 135231415-nitro-N-phenyl-1H-indole-2-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5.44 g (26.39 mmol) of 5-nitro-1H-indole-2-carboxylic acid from Example XLVII, 7.59 g (39.58 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×HCl and 1.61 g (13.19 mmol) of 4-dimethylaminopyridine are initially charged in 400 ml of a 10:1 dichloromethane:DMF mixture. 2.95 g (2.89 ml, 31.67 mmol) of aniline are added, and the mixture is stirred at RT overnight. For work-up, the mixture is diluted and extracted with aqueous hydrochloric acid and dichloromethane. The organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

  1. additionFor work-up, the mixture is diluted
  2. extractionextracted with aqueous hydrochloric acid and dichloromethane
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-da21d43823b4487d9ab6e77389d97346
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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