Water → HCID 59425037, compound

HRID 907123Notes

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) was 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 was heated to gentle reflux for 3 h, then cooled and poured into water (500 mL). The resulting precipitate was collected by filtration and taken up into ethyl acetate (300 mL). This solution was dried over Na2SO4, filtered and partially evaporated to give a precipitate, which was collected by filtration. Further evaporation and filtration gave a second crop. The two crops were 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 was heated
temperatureto gentle reflux for 3 h
temperaturecooled
filtrationThe resulting precipitate was collected by filtration
dry with materialThis solution was dried over Na2SO4
filtrationfiltered
custompartially evaporated
customto give a precipitate, which
filtrationwas collected by filtration
customFurther evaporation and filtration
customgave a second crop
customdried under vacuum

Sources & evidence

ORD record: ord-42366932f1be48e8a171542e1dbaf93b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013006B2

Reaction notes

Loading…