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

HRID 2175556Notes

Reaction equation

HRID 2175556 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-f4f76c0905b941779e16862699661864
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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