7-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 1-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

HRID 494173

Reaction equation

HRID 494173 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 125783617-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanoneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D4) (1.51 g, 5.5 mmol) and 10% palladium on charcoal (150 mg, 54% water) in methanol (80 ml) was hydrogenated at atmospheric pressure and ambient temperature for 24 h. The catalyst was removed by filtration and was washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a pale orange solid (1.29 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.05 (br, 1H), 6.95 (d, 1H), 6.54 (dd, 1H), 3.78 (m, 2H), 3.65 (br, 2H), 2.74 (br, 2H), 2.03 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. washwas washed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo

Sources & evidence

ORD record
ord-3f558095e0f045e4a530bc8a8a7e2b1f
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Linked notes

Loading…