Aniline → N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

HRID 582840Notes

Reaction equation

HRID 582840 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:11]([OH:13])=O)[C:3]1=2.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC>O1CCOCC1>[C:15]1([NH:14][C:11]([C:4]2[C:3]3[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=3[NH:6][CH:5]=2)=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153376324-Oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

Product 1

HCID 22714666N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamideYield 64.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol), aniline (0.46 mL, 5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (959 mg, 5 mmol) in 50% aqueous dioxane (10 mL) was allowed to stir at ambient temperature for 17.5 hours, then concentrated in vacuo. The residue was cooled in an ice water bath, aqueous 3.6N hydrochloric acid was added, and the precipitate collected, rinsed with aqueous 3.6N hydrochloric acid then water and dried. Recrystallization from ethyl alcohol afforded N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 35) (164 mg). mp 225-226° C.

Workup

  1. concentrationconcentrated in vacuo
  2. temperatureThe residue was cooled in an ice water bath
  3. additionaqueous 3.6N hydrochloric acid was added
  4. customthe precipitate collected
  5. washrinsed with aqueous 3.6N hydrochloric acid
  6. dry with materialwater and dried
  7. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-6d32e11502ec4e1297c0a7e4d975ab89
Source dataset
uspto-grants-1999_07
Patent number
US05925770

Reaction notes

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