Hydrochloric Acid → 5-Nitroquinolin-8-amine

HRID 1975295Notes

Reaction equation

HRID 1975295 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([NH:14]C(=O)C)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].Cl>O1CCCC1>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19099144N-(5-nitroquinolin-8-yl)acetamide

Product 1

HCID 43611555-Nitroquinolin-8-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Nitro-8-acetamidoquinoline prepared as above, (15 g, 64.9 mmol) was dissolved in tetrahydrofuran (75 ml) and treated with 40% hydrochloric acid (300 ml). The mixture was held at 80° C. for 3.5 hours and then allowed to cool. Tetrahydrofuran was removed under reduced pressure and the residual liquid was treated with saturated sodium bicarbonate solution until a neutral solution was obtained. The precipitate was removed by filtration to give 5-nitro-8-aminoquinoline (10 g).

Workup

  1. temperatureto cool
  2. customTetrahydrofuran was removed under reduced pressure
  3. additionthe residual liquid was treated with saturated sodium bicarbonate solution until a neutral solution
  4. customwas obtained
  5. customThe precipitate was removed by filtration

Sources & evidence

ORD record
ord-ca629f42b6434fba998b1b7f2964646b
Source dataset
uspto-grants-1994_02
Patent number
US05286592

Reaction notes

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