Ammonia → 4-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxamide

HRID 1896875Notes

Reaction equation

HRID 1896875 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[C:11]([C:23](OCC)=[O:24])[CH:10]=2)=[CH:5][CH:4]=1.[NH3:30]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[C:11]([C:23]([NH2:30])=[O:24])[CH:10]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58562636Ethyl 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxylate

Product 1

HCID 585628514-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxamide

Procedure

A methanolic solution of ethyl 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxylate (53 g, 131 mmol) from above step A, was cooled in an ice bath and saturated with ammonia by bubbling in ammonia. The flask was capped and stirred at room temp for 20 h. The white precipitate that formed was collected by filtration and washed with a small amount of MeOH and dried under vacuum to give the title compound.

Workup

  1. customby bubbling in ammonia
  2. customThe flask was capped
  3. customThe white precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with a small amount of MeOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0af4aa85e5064c2e9f22a3c9fca7f01b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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