Hydrochloric Acid → 7-Chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochloride

HRID 2182535Notes

Reaction equation

HRID 2182535 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1.Cl>CC(O)C.CC(C)=O>[ClH:1].[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:21][C:20]3[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][C:19]=3[F:24])=[N:3][CH:4]=[N:5]2)=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 938984-Chloro-2-fluoroanilineHCID 104904554,7-Dichloro-6-nitroquinazoline

Product 1

HCID 224782507-Chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4,7-dichloro-6-nitroquinazoline (24.4 g, 0.1 mol), 4-chloro-2-fluoroaniline and ethereal hydrogen chloride (100 ml of a 1M solution) in 2-propanol (600 ml) was heated at reflux for 1.5 hours. The mixture was allowed to cool and diluted with acetone. The solid product was collected by filtration, washed with acetone and dried to give 7-chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochloride (35.0 g, 90%) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationThe solid product was collected by filtration
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-abf127659f9e4fcf996a1274452d2c03
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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