Dimethylformamide → 6-Cyanobenz (cd)indol-2-one

HRID 1090243Notes

Reaction equation

HRID 1090243 reaction equation
Br[C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[CH:12]=[CH:13][CH:14]=2.[CH3:15][N:16](C)C=O>>[C:15]([C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[CH:12]=[CH:13][CH:14]=2)#[N:16]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 7547635-Bromo-8-naphtholactam

Product 1

HCID 150349766-Cyanobenz (cd)indol-2-one

Procedure

A mixture consisting of 9.9 grams of 6-bromobenz(cd)indol-2one, 5 grams of cuprous cyanide and 100 ml of dry dimethylformamide was stirred and heated under reflux for 20 hours. The hot mixture was filtered, and the filtrate, after cooling, gave 3.2 grams of 6-cyanobenz (cd)indol-2-one, m.p. 315° C., with decomposition. Treatment of the latter compound with 2.2 grams of phosphorous pentasulfide in 100 ml of refluxing pyridine for 18 hours, concentrating to dryness and treating with water gave 2.8 grams of crude 6-cyanobenz(cd)indol-2-thione. A portion recrystallized from acetic acid melted above 320° C. 2.8 grams of 6-cyanobenz(cd)indol-2-thione, 1.7 grams of 3-(1H-imidazolyl)propylamine, 4.2 grams of mercuric acetate, 100 ml of ethanol and 20 ml of dimethylformamide were combined and heated under reflux for 7 hours. The hot reaction mixture was filtered through diatomaceous earth, and the cake washed with 25 ml of hot dimethylformamide. The filtrate was then concentrated to dryness in vacuo. The residue was shaken with 50 ml of 5N sodium hydroxide and the mixture extracted three times with 100 ml portions of chloroform. The combined chloroform extracts were dried over sodium sulfate and the chloroform removed in vacuo. The yellow residue was recrystallized from methanol, yielding 1.9 g of N-(3-(1H-imidazol-1-yl)propyl)-2-aminobenz(cd)indol-6-carbonitrile melting at 214°C.-215° C. and analyzing as the 1/4 hydiate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe hot mixture was filtered
  4. temperaturethe filtrate, after cooling

Sources & evidence

ORD record
ord-45c04fa802c74056b7108175bcd5237a
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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