Water → HCID 18650307, compound

HRID 1613129Notes

Reaction equation

HRID 1613129 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[CH2:18][CH:17]([NH2:24])[CH2:16][CH2:15]2.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.O>CC#N.CCOCC.C(Cl)(Cl)Cl>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:24][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][C:21]([O:22][CH3:23])=[C:12]([O:11][CH3:10])[CH:13]=2)[CH2:18]1)=[O:9]

Participants

8

Reactant 4

HCID 962WaterHCID 7405L-Pyroglutamic AcidHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 9816265HCID 9816265, compound

Product 1

HCID 18650307HCID 18650307, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To L-pyroglutamic acid (1 g, 7.7 mmoles) in CH3CN (80 mL), 1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphtylamine (1.59 g, 7.7 mmoles) and EEDQ (2.85 g, 11 mmoles) were added under stirring. To the resulting mixture water was added till complete solubilization and the solution was kept at room temperature under stirring for 20 hours. The solvent was evapored and the residue taken up with CHCl3. Et2O was added under stirring. The solid which formed was filtered off giving 2 g of the title compound. Yield 81%.

Workup

  1. customwas kept at room temperature
  2. stirringunder stirring for 20 hours
  3. stirringunder stirring
  4. customThe solid which formed
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-b2ae8d7cfc954e9094b0d93259be5e91
Source dataset
uspto-grants-1993_03
Patent number
US05192759

Reaction notes

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