Diisopropylethylamine → 4-(Quinolin-2-ylmethoxy)-N1-(4-(trifluoromethyl)benzyl)benzene-1,2-diamine

HRID 1776731Notes

Reaction equation

HRID 1776731 reaction equation
[N+:1]([C:4]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:19]=[CH:18][C:5]=1[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)([O-])=O.CCN(C(C)C)C(C)C>[Pt].C1COCC1>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:20]1[CH:21]=[C:4]([NH2:1])[C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][CH:9]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 904144212-Nitro-4-(quinolin-2-ylmethoxy)-N-(4-(trifluoromethyl)benzyl)aniline

Product 1

HCID 904169694-(Quinolin-2-ylmethoxy)-N1-(4-(trifluoromethyl)benzyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 50 mL round-bottomed flask were added a stir bar, 2-nitro-4-(quinolin-2-ylmethoxy)-N-(4-(trifluoromethyl)benzyl)aniline (310 mg, 0.69 mmol), THF (6.9 mL), and DIPEA (60 μL, 0.3 mmol) followed by 5% platinum on carbon (15 mg, 0.08 mmol). The reaction vessel was evacuated and then placed under one atmosphere of hydrogen for 16 h. The mixture was then flushed with N2 and filtered through a pad of Celite. The Celite was then rinsed with additional THF (25 mL). The resulting solution was concentrated to dryness to afford the title compound which was used without further purification. MS (ESI): mass calcd. for C24H20F3N3O, 423.16; m/z found, 424.1 [M+H]+.

Workup

  1. additionTo a 50 mL round-bottomed flask were added a stir bar
  2. customThe reaction vessel was evacuated
  3. customThe mixture was then flushed with N2
  4. filtrationfiltered through a pad of Celite
  5. washThe Celite was then rinsed with additional THF (25 mL)
  6. concentrationThe resulting solution was concentrated to dryness

Sources & evidence

ORD record
ord-2598a265936f47278d67ae63dff69c50
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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