Methyl 3,3-dimethoxypropionate → Methyl 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarboxylate

HRID 1656438Notes

Reaction equation

HRID 1656438 reaction equation
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=O.[CH3:19][O:20][CH:21]([O:27]C)[CH2:22][C:23](OC)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[C:2](=[C:16]([CH3:17])[CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:1]=[CH:23][C:22]=1[C:21]([O:20][CH3:19])=[O:27]

Participants

5

Reactant 3

HCID 81924Methyl 3,3-dimethoxypropionateHCID 521998p-Toluenesulfonic acid monohydrateHCID 149185372-Amino-2'-chloro-3,5-dimethylbenzophenone

Product 1

HCID 10245799Methyl 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarboxylateYield 58.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-amino-2'-chloro-3,5-dimethylbenzophenone (2.59 g), methyl 3,3-dimethoxypropionate (3.7 g), p-toluenesulfonic acid hydrate (0.19 g) and benzene (30 ml) was refluxed for 16 hrs., with removal of water by a Dien-Stark apparatus. The mixture was distilled to remove the solvent, and the residue was purified by a column chromatography on silica gel to give methyl 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarboxylate as crystals (1.90 g, 58.5%), which was recrystallized from isopropyl ether as colorless prisms. m.p. 117°-118° C.

Workup

  1. temperaturewas refluxed for 16 hrs
  2. custom, with removal of water by a Dien-Stark apparatus
  3. distillationThe mixture was distilled
  4. customto remove the solvent
  5. customthe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-4d92eb3541bf4eab8e517dfe885d966d
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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