Potassium sodium tartarate → HCID 18462076, compound

HRID 2303960Notes

Reaction equation

HRID 2303960 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][CH2:20][CH2:21][C:13]3=[C:12]([CH:22]=[C:23]([N+:25]([O-])=O)[CH3:24])[C:11]=2[CH2:10]1.[C:28]([CH:31]([CH:33]([C:35]([O-:37])=[O:36])O)O)([O-:30])=[O:29].[Na+].[K+]>O1CCCC1>[C:35]([OH:37])(=[O:36])/[CH:33]=[CH:31]/[C:28]([OH:30])=[O:29].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH2:21][C:13]1=[C:12]2[CH2:22][CH:23]([NH2:25])[CH3:24]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 69849323HCID 69849323, compound

Product 1

HCID 18462076HCID 18462076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium aluminium hydride in tetrahydrofuran under argon is added dropwise a solution of 1-(2-methoxy-6,7,8,9-tetrahydro-1H-pyrido[1,2-a]indol-10-yl)-2-nitro-1-propene in tetrahydrofuran. The mixture is heated under reflux for 4 h and cooled to 0° C. To the mixture is added dropwise aqueous potassium sodium tartrate solution and the mixture is stirred for 30 min and filtered through kieselguhr. The filtrate is extracted with dichloromethane. The combined organic extracts are washed (water, brine), dried (sodium sulfate), concentrated in vacuo, dissolved in hot 2-propanol and added dropwise to a stirred solution of fumaric acid in 2-propanol at 50° C. The mixture is cooled to 0° C. and filtered. The filter-cake is washed (2-propanol, ether) and dried to give the product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 h
  3. filtrationfiltered through kieselguhr
  4. extractionThe filtrate is extracted with dichloromethane
  5. washThe combined organic extracts are washed (water, brine)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. dissolutiondissolved in hot 2-propanol
  9. additionadded dropwise to a stirred solution of fumaric acid in 2-propanol at 50° C
  10. temperatureThe mixture is cooled to 0° C.
  11. filtrationfiltered
  12. washThe filter-cake is washed (2-propanol, ether)
  13. customdried
  14. customto give the product

Sources & evidence

ORD record
ord-6055e1f72e954d6886fb5ea825b2da0c
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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