Trifluoroacetic acid → HCID 10362064, compound

HRID 1033504Notes

Reaction equation

HRID 1033504 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1(O)[CH2:18][CH2:17][CH2:16][C:15]2[N:14]=[C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[CH:11][C:10]1=2.[C:28]1([CH2:34][O:35][NH2:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH3:8][C:9]1([NH:36][O:35][CH2:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][CH2:17][CH2:16][C:15]2[N:14]=[C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 102313O-BenzylhydroxylamineHCID 10061627HCID 10061627, compound

Product 1

HCID 10362064HCID 10362064, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (17.4 g) was added in one portion to a solution of 5,6,7,8-tetrahydro-5-methyl-2-(phenylmethoxy)-quinolin-5-ol (41 g), phenylmethoxyamine (47 g), and toluene (770 ml) at room temperature. The solution was stirred at room temperature for 24 hrs, and then quenched with concentrated ammonium hydroxide solution. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated. Purification by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) gave 44.2 g (77%) of 5,6,7,8-tetrahydro-5-methyl-N,2-bis(phenylmethoxy)-5-quinolinamine.

Workup

  1. customquenched with concentrated ammonium hydroxide solution
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customPurification
  9. washby high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-e5d193cd859a46cc963d998cc1f6e312
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

Loading…