4-Ethoxyaniline → HCID 54510564, compound

HRID 582842Notes

Reaction equation

HRID 582842 reaction equation
[N+:1]([C:4]1[NH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:16])[C:11]=2[C:12]=1[C:13]([OH:15])=O)([O-:3])=[O:2].[CH3:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=1.Cl.CN(C)CCCN=C=NCC>O1CCOCC1>[CH2:18]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:13]([C:12]2[C:11]3[C:10](=[O:16])[CH2:9][CH2:8][CH2:7][C:6]=3[NH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[O:15])=[CH:24][CH:25]=1)[CH3:17]

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18696537HCID 18696537, compound

Product 1

HCID 54510564HCID 54510564, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-nitro-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (0.18 g, 0.8 mmol), p-phenetidine (0.52 mL, 4 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (767 mg, 4 mmol) in 50% aqueous dioxane (10 mL) was stirred for 67 hours, then concentrated in vacuo. Aqueous 3.6N hydrochloric acid was added, the mixture cooled in an ice water bath, and the precipitate collected, rinsed with water then diethyl ether, and dried. Purification on Silica gel (10% methyl alcohol/dichloromethane) gave N-(4-ethoxyphenyl)-2-nitro-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 56) (51 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. additionAqueous 3.6N hydrochloric acid was added
  3. temperaturethe mixture cooled in an ice water bath
  4. customthe precipitate collected
  5. washrinsed with water
  6. dry with materialdiethyl ether, and dried
  7. customPurification on Silica gel (10% methyl alcohol/dichloromethane)

Sources & evidence

ORD record
ord-74b921919c3141cfbf0fd7e53f718b5c
Source dataset
uspto-grants-1999_07
Patent number
US05925770

Reaction notes

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