5-Aminoindole → 4-(1H-Indol-5-ylamino)-6-nitro-quinoline-3-carbonitrile

HRID 1595766Notes

Reaction equation

HRID 1595766 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[NH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2>C(O)C>[NH:23]1[C:24]2[C:20](=[CH:19][C:18]([NH:17][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:15]#[N:16])=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

4

Reactant 2

HCID 788675-AminoindoleHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 217047944-(1H-Indol-5-ylamino)-6-nitro-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 200 ml ethanol, and 3.40 g (25.8 mmol) 5-aminoindole was heated to reflux under N2 for 3.5 hours. Removed heat, made basic with saturated sodium bicarbonate and stripped solvents, azeotroping with ethanol. Collected solids and washed with hexane, then water. Dissolved solids in 200 ml ethyl acetate, added Darco and filtered. Stripped solvent and dried in vacuo overnight (50° C.). Washed twice more with ether to removed starting material aminoindole. 4.372 g of red-brown solid: mass spectrum (m/e electrospray): M+H=330.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 3.5 hours
  3. customRemoved
  4. temperatureheat
  5. customazeotroping with ethanol
  6. customCollected solids
  7. washwashed with hexane
  8. dissolutionDissolved solids in 200 ml ethyl acetate
  9. additionadded Darco
  10. filtrationfiltered
  11. customStripped solvent and dried in vacuo overnight (50° C.)
  12. washWashed twice more with ether
  13. customto removed

Sources & evidence

ORD record
ord-90d5e82c75384bfdbd1e870bd8053aee
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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