5-Amino-4-fluoro-2-methylphenol → 6-Chloro-4-(2-fluoro-5-hydroxy-4-methylanilino)cinnoline hydrochloride

HRID 1057355Notes

Reaction equation

HRID 1057355 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[F:13][C:14]1[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[CH:17][C:15]=1[NH2:16]>CC(O)CCC.Cl>[ClH:1].[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[N:4][CH:3]=[C:2]2[NH:16][C:15]1[CH:17]=[C:18]([OH:22])[C:19]([CH3:21])=[CH:20][C:14]=1[F:13]

Participants

5

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 124480754,6-Dichlorocinnoline

Product 1

HCID 219910536-Chloro-4-(2-fluoro-5-hydroxy-4-methylanilino)cinnoline hydrochlorideYield 95.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 223862-PentanolSolvent

Procedure

A solution of 4,6-dichlorocinnoline (200 mg, 1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (169 mg, 1.2 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (4 ml) containing 7M isopropanolic hydrogen chloride (2 drops) was heated at reflux for 45 minutes. After cooling the solid was filtered off, washed with isopropanol followed by ether to give 6-chloro-4-(2-fluoro-5-hydroxy-4-methylanilino)cinnoline hydrochloride (326 mg, 95%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. temperatureAfter cooling the solid
  4. filtrationwas filtered off
  5. washwashed with isopropanol

Sources & evidence

ORD record
ord-fb122a2d26e24147991ff719253f31c2
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

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