Water → HCID 59425037, compound

HRID 1009553Notes

Reaction equation

F[C:2]1C=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1N.[C:12](#[N:16])[CH2:13][C:14]#[N:15].[C:17](=O)([O-])[O-].[K+].[K+].O.[CH3:24][N:25]([CH3:28])C=O>>[NH2:15][C:14]1[N:25]([CH2:28][CH3:17])[C:24]2[C:2]([C:13]=1[C:12]#[N:16])=[CH:3][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=2

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 8010Malononitrile

HCID 11430Potassium Carbonate

HCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 59425037HCID 59425037, compoundYield 52%

Procedure

A solution of 2-fluoro-5-nitroaniline (11.7 g, 74.9 mmol) in dimethylformamide (120 mL) is treated with malononitrile (5.28 g, 80.0 mmol) and potassium carbonate (11.05 g, 80.0 mmol) (Modification of Chem. Heterocyclic Cpd. Engl. Trans., 9, 37 (2001)). The resulting heterogeneous mixture is heated to gentle reflux for 3 h, then cooled and poured into water (500 mL). The resulting precipitate is collected by filtration and taken up into ethyl acetate (300 mL). This solution is dried over Na2SO4, filtered and partially evaporated to give a precipitate, which is collected by filtration. Further evaporation and filtration give a second crop. The two crops are combined and dried under vacuum to give 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (7.90 g, 52%) as an orange powder.

Workup

temperatureThe resulting heterogeneous mixture is heated
temperatureto gentle reflux for 3 h
temperaturecooled
filtrationThe resulting precipitate is collected by filtration
dry with materialThis solution is dried over Na2SO4
filtrationfiltered
custompartially evaporated
customto give a precipitate, which
filtrationis collected by filtration
customFurther evaporation and filtration
customgive a second crop
customdried under vacuum

Sources & evidence

ORD record: ord-0fd583ca39e349f8b2f114f82c81432f
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973069B2

Reaction notes

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