Quinoline → HCID 67408045, compound

HRID 1044464Notes

Reaction equation

HRID 1044464 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[O:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[C:17]([O:22]C)[CH:16]=[C:15]([O:24]C)[C:14]=2[C@@H:26]1[CH2:30][CH2:29][N:28]([CH3:31])[C@H:27]1[CH2:32][OH:33].Cl.N1C=CC=CC=1.N1C2C(=CC=CC=2)C=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[O:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[C:17]([OH:22])[CH:16]=[C:15]([OH:24])[C:14]=2[C@@H:26]1[CH2:30][CH2:29][N:28]([CH3:31])[C@H:27]1[CH2:32][OH:33]

Participants

6

Reactant 4

HCID 7047QuinolineHCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 68513538HCID 68513538, compound

Product 1

HCID 67408045HCID 67408045, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (−)-trans-2-(2-chloro-4-nitrophenyl)-8-(2-hydroxymethyl-1-methyl pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one (0.4 g, 0.8 mmol), pyridine hydrochloride (0.48 g, 4.1 mmol) and a catalytic amount of quinoline was heated at 180° C. for a period of 2 hrs. The reaction mixture was cooled and diluted with methanol (50 mL) and basified with solid Na2CO3 to pH 10. The reaction mixture was filtered, and washed with methanol. The organic layer was concentrated and the residue purified by column chromatography using 0.1% ammonia and 3% methanol in chloroform as eluent to yield the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe reaction mixture was filtered
  3. washwashed with methanol
  4. concentrationThe organic layer was concentrated
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-52fad680944f4fcf8af67f9dcc252929
Source dataset
uspto-grants-2013_10
Patent number
US08563596B2

Reaction notes

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