Hydrochloric Acid → Quinoline

HRID 1387677Notes

Reaction equation

HRID 1387677 reaction equation
Cl.Cl.[N+]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)([O-])=O.Cl.[N+](C1C=CC=C2C=1N=CC=C2)([O-])=O>C(OCC)(=O)C.CN(C)C=O>[N:11]1[C:12]2[C:7](=[CH:6][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 17764984HCID 17764984, compoundHCID 17764985HCID 17764985, compound

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A crude nitration mixture (50 g) created in the manner of Preparation I was dissolved in 500 mL of ethyl acetate. Approximately 10.4 g (0.29 mole) of hydrogen chloride gas was added giving a yellow precipitate. (Note: The amount of hydrogen chloride gas added could only be approximated as it was measured by weighing the flask.) This precipitate was analyzed and found to contain 5-nitroquinoline hydrochloride and 8-nitroquinoline hydrochloride in a ratio of 51:41. The precipitate was collected by filtration and dried affording 54 g. The crude product was suspended in 270 mL of wet dimethylformamide (0.5 parts water in 99.5 parts dimethylformamide) to form a slurry. The slurry was heated to dissolution (95° C.-100° C.) to form a solution and this solution was cooled to 25° C. Crystallization of a cream colored solid commenced at about 85° C.-95° C. The solid was collected by filtration, washed with ethyl acetate (2×25 mL) and dried and found to be 99.0% 5-nitroquinoline hydrochloride and 0.41% 8-nitroquinoline hydrochloride. The yield of 5-nitroquinoline hydrochloride was 20.8 g (34.5% overall yield from quinoline).

Workup

  1. customgiving a yellow precipitate
  2. filtrationThe precipitate was collected by filtration
  3. customdried
  4. customaffording 54 g
  5. customto form a slurry
  6. temperatureThe slurry was heated to dissolution (95° C.-100° C.)
  7. customto form a solution
  8. customCrystallization of a cream
  9. customcommenced at about 85° C.-95° C
  10. filtrationThe solid was collected by filtration
  11. washwashed with ethyl acetate (2×25 mL)
  12. customdried

Sources & evidence

ORD record
ord-88f5afd1a3b6460b8d810badb87dad3b
Source dataset
uspto-grants-2001_07
Patent number
US06268500B1

Reaction notes

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