2,2,2-trifluoro-1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone → 1-(7-Amino-3,4-dihydroisoquinolin-2(1H)-YL)-2,2,2-trifluoroethanone

HRID 1157561Notes

Reaction equation

HRID 1157561 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[F:18][C:15]([F:16])([F:17])[C:14]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11]1)=[O:19]

Participants

4

Reactant 1

HCID 219568152,2,2-trifluoro-1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Product 1

HCID 107527801-(7-Amino-3,4-dihydroisoquinolin-2(1H)-YL)-2,2,2-trifluoroethanoneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-Nitro-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (15 g, 54.7 mmol) was stirred vigorously in EtOAc (50 mL) with 5% Pd/C (1.5 g) under hydrogen gas (1 atmosphere) for 15 h and then filtered through celite. The filtrate was concentrated under vacuum and yielded 11.2 g (84%) of the tan solid 2-(trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinamine. 1H NMR (400 MHz, DMSO-d6) δ 6.84-6.79 (m, 1H), 6.46-6.40 (m, 1H), 6.35 (m, 1H), 4.95 (s, 2H), 4.56 (s, 2H), 3.76-3.68 (m, 2H), 2.74-2.66 (m, 2H).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f3ef30eabd2647268e45d9a0f652f6ef
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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