Ethyl formate → HCID 86733854, compound

HRID 1283822Notes

Reaction equation

HRID 1283822 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[H-].[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[CH:14](C)[CH2:13][C:12]2=[O:29].C(OCC)=O>C1C=CC=CC=1.C(O)C>[OH:1][CH:2]=[C:3]1[C:12](=[O:29])[C:11]2[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([O:8][CH3:7])[CH:10]=2)[N:15]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[CH:14]1[CH3:13]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 21439716Butyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 86733854HCID 86733854, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To sodium ethoxide freshly prepared from 4.8 g. of sodium hydride and 6.0 ml. of ethanol is added 16.0 g. of butyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate and 19.8 ml. of ethyl formate in 150 ml. of benzene over a 30 min. period. The reaction mixture, after stirring at room temperature for 4 hrs., is poured onto 250 ml. of ice-water. The aqueous layer is retained and the organic layer extracted with 1N aqueous sodium hydroxide. The base extracted is combined with the separated aqueous and backwashed with benzene. The aqueous layer is then added to 250 ml. of 12N hydrochloric acid. The resulting yellow oil is extracted with chloroform and the chloroform layer dried over magnesium sulfate. The solvent is removed under reduced pressure and the residual product used in subsequent reactions without further purification.

Workup

  1. addition, is poured onto 250 ml
  2. extractionthe organic layer extracted with 1N aqueous sodium hydroxide
  3. extractionThe base extracted
  4. additionThe aqueous layer is then added to 250 ml
  5. extractionThe resulting yellow oil is extracted with chloroform
  6. dry with materialthe chloroform layer dried over magnesium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe residual product used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-c3b198f9e001477d9fbd1430dc75536e
Source dataset
uspto-grants-1976_08
Patent number
US03976650

Reaction notes

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