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

HRID 2178438
Notes
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Reaction equation

HRID 2178438 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-fb1ed38d3fb7498cae6fe49543ed5281
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067917B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes