Dichloromethane → Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

HRID 2105544Notes

Reaction equation

HRID 2105544 reaction equation
[O:1]=[C:2]1[CH:11]([CH2:12][C:13]([OH:15])=[O:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH3:16]CN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.C(Cl)Cl>CO>[CH3:16][O:14][C:13](=[O:15])[CH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183329702-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acid

Product 1

HCID 21519358Methyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2-Oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid (2.73 mmol), EDCl (3.27 mmol) and DIEA (3.27 mmol) are dissolved in 10 mL MeOH. About 2 mL of CH2Cl2 is also added to help dissolving the solid. The reaction mixture is stirred at room temperature for 2 hours before removal of the solvent under reduced pressure. The residue is purified by silica gel chromatography (hexane/EtOAc) to give (2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid methyl ester as a white solid. Yield: 60%. 1H NMR (400 MHz, CDCl3): δ 7.88 (br, 1H), 7.18 (m, 2H), 7.00 (td, 1H), 6.75 (d, 1H), 3.73 (s, 3H), 3.13-2.98 (m, 3H), 2.89 (m, 1H), 2.51 (dd, 1H). MS: (ES+): 220.2 [M+1].

Workup

  1. dissolutionto help dissolving the solid
  2. customThe residue is purified by silica gel chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-86dd02f8cf554c1a835d294d70d3ad7f
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

Loading…