6-Chloro-8-nitroquinoline → 6-Chloro-8-aminoquinoline

HRID 2241992Notes

Reaction equation

HRID 2241992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 1104626-Chloro-8-nitroquinoline

Product 1

HCID 796186-Chloro-8-aminoquinolineYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a hot suspension of 6-chloro-8-nitroquinoline (Mosher, et al., Org. Syn. 27:48 (1947), 0.8 g) in a mixture of ethanol/glacial acetic acid/water (2:2:1, 25 mL) was added iron powder (0.5 g) portionwise. The resulting mixture was stirred at reflux for 1.5 hours. The reaction was the cooled to room temperature, filtered through celite and made basic by addition of solid Na2CO3. The aqueous mixture was extracted with Et2O. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator to give the desired product (0.5 g) as a yellow solid; MP. 70-73° C.; MS (ES) m/z (relative intensity) 179 (M+H)+ (100).

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationfiltered through celite
  3. additionmade basic by addition of solid Na2CO3
  4. extractionThe aqueous mixture was extracted with Et2O
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-4c4de8fbb27d4635a9b48dc328d8409e
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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