Triethylamine → (2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-ol

HRID 1663451Notes

Reaction equation

HRID 1663451 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[NH2:16][C@@H:17]([CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][OH:19].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:22]([O:21][CH2:20][C@H:17]([NH:16][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH2:18][OH:19])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 17998970(2R)-2-amino-3-(benzyloxy)propan-1-ol hydrochloride

Product 1

HCID 59828596(2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-olYield 81.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitroquinoline (41.0 g, 197 mmol) was added to a mixture of (2R)-2-amino-3-(benzyloxy)propan-1-ol hydrochloride (43.0 g, 197 mmol) and triethylamine (69.0 mL, 494 mmol) dissolved in 985 mL of CH2Cl2 at 0° C. The resulting yellow mixture was stirred for 18 hours at ambient temperature. The solvent was then removed under reduced pressure to afford a yellow solid. The solid was stirred in H2O (100 mL) and filtered to give 57 g of (2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-ol as a bright yellow solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customto afford a yellow solid
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4cbeeb2ecda74ea793e5f9f6ae79bdf5
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

Loading…