Hydrochloric Acid → HCID 58998228, compound

HRID 1592945Notes

Reaction equation

HRID 1592945 reaction equation
Cl.C(O)C.[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[N+:25]([O-])=O.[OH-].[Na+]>C(OCC)(=O)C>[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[NH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 17864581HCID 17864581, compound

Product 1

HCID 58998228HCID 58998228, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Reduced iron (84.2 g, 1.51 mol) and 1.5 mol/L hydrochloric acid (605 mL) were added to ethanol (2.5 L) and the mixture was heated to 90° C. with stirring. To this mixture was added (7-bromo-6-nitro-4-quinazolinyl)-(3-chloro-4-fluorophenyl)amine 4 times (30 g each time) every 30 min. The mixture was heated under reflux for 5 hrs and the inner temperature was set to 50° C. 2N Aqueous sodium hydroxide solution (450 mL) and 1N aqueous sodium hydroxide solution were added to adjust the pH thereof to 7-8 and the mixture was stirred for a while. Ethyl acetate (1 L) and Celite (300 g) were added, and after stirring for a while, the mixture was filtered through Celite. The residue was washed with THF-ethyl acetate (1:1, 1 L) and the filtrate was concentrated under reduced pressure. Water (1 L) was added to the concentrate and the product was collected by filtration and dried under reduced pressure at 60° C. overnight to give the title compound (108.76 g, 98%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customwas set to 50° C
  4. stirringto 7-8 and the mixture was stirred for a while
  5. stirringafter stirring for a while
  6. filtrationthe mixture was filtered through Celite
  7. washThe residue was washed with THF-ethyl acetate (1:1, 1 L)
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionWater (1 L) was added to the
  10. concentrationconcentrate
  11. filtrationthe product was collected by filtration
  12. customdried under reduced pressure at 60° C. overnight

Sources & evidence

ORD record
ord-f92c644e606444fc86d32aa316af056d
Source dataset
uspto-grants-2007_11
Patent number
US07294629B2

Reaction notes

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