8-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-6-nitro-1,2,3,4-tetrahydroquinoline → 8-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine

HRID 1922477Notes

Reaction equation

HRID 1922477 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:20]([O-])=O)[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2.[H][H]>O1CCCC1.C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 2

HCID 598070798-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-6-nitro-1,2,3,4-tetrahydroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 598070738-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amineYield 99.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-6-nitro-1,2,3,4-tetrahydroquinoline (660 mg, 2.147 mmol) in tetrahydrofuran (6 ml) and ethanol (6.00 ml) was added palladium on carbon, 10 wt % (229 mg, 0.215 mmol). The suspension was stirred under balloon pressure of hydrogen and monitored by TLC. After 4 h, the reaction was complete. The mixture was then filtered through a pad of celite which was washed with methanol. The filtrate was then concentrated and dried on a high vacuum pump. The residue (8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine (590 mg, 2.127 mmol, 99% yield)) was used directly in the subsequent reaction. 1H NMR (DMSO-d6) δ 6.16 (dd, J=14.7, 2.4 Hz, 1H); 6.04 (m, 1H), 4.70 (brs, 1H), 2.99-2.93 (m, 3H), 2.88-2.82 (m, 2H), 2.57-2.53 (m, 2H), 2.24 (s, 3H), 2.15-2.05 (m, 2H); 1.93-1.87 (m, 2H), 1.69-1.60 (m, 4H), 1.44-1.35 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through a pad of celite which
  2. washwas washed with methanol
  3. concentrationThe filtrate was then concentrated
  4. customdried on a high vacuum pump

Sources & evidence

ORD record
ord-05986c7aaea64ae78be7226121ee59e6
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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