N,N-Dimethyl-2-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine → 7-Amino-1-(2-dimethylaminoethyl)-1,2,3,4-tetrahydroquinoline

HRID 1922407Notes

Reaction equation

HRID 1922407 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7][CH2:6]1>C(O)C.[Pd]>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 58874105N,N-Dimethyl-2-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine

Product 1

HCID 283433417-Amino-1-(2-dimethylaminoethyl)-1,2,3,4-tetrahydroquinolineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 4 (0.8 g, 3.208 mmol) in dry ethanol (20 mL) was treated with Pd—C (˜0.08 g) and purged with hydrogen gas. The reaction was stirred at room temperature under hydrogen atm. for 3 h. The reaction was filtered through celite bed and washed with methanol (3×20 mL). The combined organic layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 5 (0.6 g, 86%).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with methanol (3×20 mL)
  4. customThe combined organic layer was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-f6adbcc1b33444cfa2c74d4eacb83a3d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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