Hydrochloric Acid → HCID 22646535, compound

HRID 393669Notes

Reaction equation

HRID 393669 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=1.Cl.CCOCC>C(O)(C)C>[ClH:19].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:27][C:26]3[CH:28]=[CH:29][C:23]([Cl:22])=[CH:24][C:25]=3[F:30])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 938984-Chloro-2-fluoroanilineHCID 226465197-Benzyloxy-4-chloro-6-cyanoquinoline

Product 1

HCID 22646535HCID 22646535, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 7-benzyloxy-4-chloro-6-cyanoquinoline (2 g, 6.8mmol), 4-chloro-2-fluoroaniline (1.1 g, 7.5 mmol) in isopropanol (50 ml) containing 1M ethereal hydrogen chloride (8 ml) was heated at reflux for 2 hours. After cooling to ambient temperature ether was added. The precipitate was collected by filtration, washed with isopropanol, followed by ether and dried under vacuum to give 7-benzyloxy-4-(4-chloro-2-fluoroanilino)-6-cyanoquinoline hydrochloride (2.41 g, 81%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with isopropanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-add145f94cf8478a921a9eb6aac229f7
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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