Ethyl formate → 3-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, methyl ester

HRID 328813Notes

Reaction equation

HRID 328813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:15]([O:17][CH3:18])=[O:16])[CH:8]([CH3:19])[CH2:7][C:6]2=[O:20].[CH:21](OCC)=[O:22].[O-]CC.[Na+].[H-].[Na+]>C(O)C.C1C=CC=CC=1>[OH:22][CH:21]=[C:7]1[C:6](=[O:20])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]([C:15]([O:17][CH3:18])=[O:16])[CH:8]1[CH3:19]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 21439723Methyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 867338533-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

Methyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate (13.8 g.) in 140 ml. of benzene containing 19 ml. of ethyl formate is added to sodium ethoxide freshly prepared from 4.8 g. of sodium hydride and 6 ml. of ethanol over a period of 45 min. After stirring at room temperature for 4 hrs. the reaction mixture is poured onto 250 ml. of ice-water. The aqueous layer is retained and the organic layer washed with 1N aqueous sodium hdyroxide. The washings are combined with the aqueous extracts and backwashed with benzene. The aqueous layer is then made acid with 12N hdyrochloric acid and extracted with chloroform. The organic phase is separated, dried over magnesium sulfate and evaporated in vacuo to dryness. The residue is employed in subsequent reactions without further purification.

Workup

  1. customfreshly prepared from 4.8 g
  2. additionthe reaction mixture is poured onto 250 ml
  3. washthe organic layer washed with 1N aqueous sodium hdyroxide
  4. extractionextracted with chloroform
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo to dryness
  8. customThe residue is employed in subsequent reactions without further purification

Sources & evidence

ORD record
ord-a497f81fb3194ca0a90c55877d29ed5d
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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