Triethylamine → 3-Amino-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline

HRID 1512114Notes

Reaction equation

HRID 1512114 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:9][CH:8]=2)([O-])=O.C(N(CC)CC)C>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 595075993-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline

Product 1

HCID 595079823-Amino-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline (134 mg, 0.46 mmol) was dissolved in EtOAc (10 mL) and the solution was sparged with N2 for several minutes. Triethylamine (0.065 mL, 0.46 mmol) was then added followed by a catalytic amount of 10% Pd/C. Sparging with N2 was repeated after each addition. A balloon of H2 was connected to the reaction flask and the reaction mixture was stirred at room temperature under H2 atmosphere for 48 hours. The mixture was then filtered through a Celite pad and concentrated to obtain crude 3-amino-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline, which was used as is in the next reaction. LC/MS (m/z): 258.1 (MH+), Rt 0.33 minutes.

Workup

  1. customthe solution was sparged with N2 for several minutes
  2. customSparging with N2
  3. additionafter each addition
  4. filtrationThe mixture was then filtered through a Celite pad
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c040819d239f48b9bf4484a6ce987614
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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