Hydrochloric Acid → HCID 20067180, compound

HRID 358852Notes

Reaction equation

HRID 358852 reaction equation
C([O:3][C:4]([C:6]1[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=[C:8]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1)=[O:5])C.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].O>[O:18]([CH2:17][C:8]1[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 54400604HCID 54400604, compound

Product 1

HCID 20067180HCID 20067180, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

42 g of 6-phenoxymethylpyridine-2,3-dicarboxylic acid diethyl ester are added to a solution of 0.5 g of tetrabutylammonium bromide in 140 ml of 15% aqueous sodium hydroxide solution while stirring. The resulting suspension is heated to 80° and stirred for one hour. The reaction mixture is then diluted with 300 ml of water and the solution is acidified to pH 2 using concentrated hydrochloric acid, during the course of which a precipitate forms which is filtered off with suction. The filtration residue is stirred with methylene chloride/tetrahydrofuran and filtered. The filtrate is dried over magnesium sulphate, concentrated and combined with the contents of the suction filter. After the whole has been dried again over phosphorus pentoxide, 34 g of the above acid, having a melting point of 270° with decomposition, are obtained.

Workup

  1. temperatureThe resulting suspension is heated to 80°
  2. stirringstirred for one hour
  3. filtrationduring the course of which a precipitate forms which is filtered off with suction
  4. stirringThe filtration residue is stirred with methylene chloride/tetrahydrofuran
  5. filtrationfiltered
  6. dry with materialThe filtrate is dried over magnesium sulphate
  7. concentrationconcentrated
  8. filtrationfilter
  9. dry with materialAfter the whole has been dried again over phosphorus pentoxide, 34 g of the above acid
  10. customare obtained

Sources & evidence

ORD record
ord-9ba21017d27f449ea507aea16b1a54b9
Source dataset
uspto-grants-1991_03
Patent number
US04997947

Reaction notes

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