Hydrazine → 6-Amino-4-(1H-indol-5-ylamino)-quinoline-3-carbonitrile

HRID 1595822Notes

Reaction equation

HRID 1595822 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=4)[N:14]=[CH:13][C:12]=3[C:24]#[N:25])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.NN>[Pd].C(O)C>[NH2:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:24]#[N:25])=[C:11]2[NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 217047944-(1H-Indol-5-ylamino)-6-nitro-quinoline-3-carbonitrile

Product 1

HCID 98574636-Amino-4-(1H-indol-5-ylamino)-quinoline-3-carbonitrileYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Covered 200 mg of 10% Palladium on carbon with 75 ml ethanol. Added 2.00 g (6.07 mmol) 4-(1H-indol-5-ylamino)-6-nitro-quinoline-3-carbonitrile and 477 μl (15.2 mmol) hydrazine. Heated to reflux under N2 for 2 hours. Filtered hot through celite and washed through with hot methanol. Removed solvent and dried in vacuo (50° C.), giving 1.89 g brown solid: mass spectrum (m/e electrospray): M+H=300.2.

Workup

  1. temperatureHeated
  2. temperatureto reflux under N2 for 2 hours
  3. filtrationFiltered hot through celite
  4. washwashed through with hot methanol
  5. customRemoved solvent and dried in vacuo (50° C.)

Sources & evidence

ORD record
ord-ebc53e334fad4a409861766b477b54a8
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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