Citric Acid → HCID 131713638, compound

HRID 358152Notes

Reaction equation

HRID 358152 reaction equation
[CH2:1]([C:3]1([CH2:20][C:21]([C:24]([O:26]C)=[O:25])=[N:22][OH:23])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+].C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH2:1]([C:3]1([CH2:20][C:21]([C:24]([OH:26])=[O:25])=[N:22][OH:23])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 73808676HCID 73808676, compound

Product 1

HCID 131713638HCID 131713638, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 9.25 g. (0.025 mole) of (+)-ethyl-1-(2'-methoxycarbonyl-2'-hydroxyimino-ethyl)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine, 8.0 g (0.2 mole) of solid sodium hydroxide, 100 ml. of ethanol and 5.0 ml. of water is acidified to a pH value of 6.3 by the addition of a solution of 16 g. of citric acid in 150 ml. of water. The solution is extracted six times with 50 ml. of dichloromethane each. The united organic phases are extracted with a saturated sodium chloride solution, the layers are separated, the organic phase is dried over anhydrous sodium sulfate, filtered and the filtrate is evaporated. To the residue 50 ml. of ether are added, the mixture is heated to boiling, then cooled, the precipitated product is filtered and dried. Thus 7.2 g. of the named compound are obtained, yield 81%. Mp.: 124° C. (decomposition).

Workup

  1. additionA mixture of 9.25 g
  2. extractionThe solution is extracted six times with 50 ml
  3. extractionThe united organic phases are extracted with a saturated sodium chloride solution
  4. customthe layers are separated
  5. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. additionof ether are added
  9. temperaturethe mixture is heated
  10. temperaturecooled
  11. filtrationthe precipitated product is filtered
  12. customdried
  13. customof the named compound are obtained

Sources & evidence

ORD record
ord-aec7b0c3fd9146189518b2234761f4a8
Source dataset
uspto-grants-1984_08
Patent number
US04464535

Reaction notes

Loading…