Methanol → Methyl 7-chloro-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxylate

HRID 922809Notes

Reaction equation

HRID 922809 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[F:22])=[CH:7][C:8]([C:12]#N)=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:24][OH:25].C[OH:27]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[F:22])=[CH:7][C:8]([C:12]([O:25][CH3:24])=[O:27])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 21893726Hydrochloride methanolHCID 895435847-Chloro-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carbonitrile

Product 1

HCID 89543854Methyl 7-chloro-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxylateYield 90%

Conditions

Temperature
60 °C

Procedure

7-Chloro-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carbonitrile (4.4 g, 14.07 mmol) was suspended in MeOH (70.3 ml), added 200 ml sat HCl/MeOH and then heated to 60° C. for 4 hours. The reaction was allowed to cool to ambient temperature and then was concentrated. The residue was dissolved in EtOAc and then washed with 1:1 1N NaOH/sat NaHCO3, brine, dried (MgSO4) and concentrated to afford methyl 7-chloro-4-(2-fluoro-4-methoxyphenyl)quinoline-2-carboxylate (4.4 g, 12.73 mmol, 90% yield) as a yellow solid.

Workup

  1. additionadded 200 ml
  2. temperatureto cool to ambient temperature
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 1:1 1N NaOH/
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c4b00f3c03664dcaacf8cf11ca62f7bf
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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