Water → HCID 19089117, compound

HRID 1463981Notes

Reaction equation

HRID 1463981 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH:8](OCC)[O:9][CH2:10][CH3:11])[N:5]=[CH:4][C:3]=1[C:15](O)=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-].ClCCl.O>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:6](/[CH:7]=[CH:8]/[O:9][CH2:10][CH3:11])[N:5]=[CH:4][C:3]=1[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11139333HCID 11139333, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 19089117HCID 19089117, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

To a suspension of 5-amino-4-carboxy-1-(2,2-diethoxyethyl)pyrazole (4 g) in xylene (15.6 ml) was added dropwise 3.4M solution of sodium bis(2-methoxyethoxy)-aluminum hydride in toluene (15.6 ml) at room temperature in an atmosphere of nitrogen. Then the mixture was refluxed for 6 hours, and poured into a mixture of dichloromethane and water. The precipitate was filtered off, and the organic layer was separated and dried over magnesium sulfate. The organic solvent was evaporated in vacuo to give 5-amino-4-methyl-1-[(E)-2-ethoxyvinyl]-pyrazole (598 mg).

Workup

  1. temperatureThen the mixture was refluxed for 6 hours
  2. filtrationThe precipitate was filtered off
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customThe organic solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1b4fa93c714647ffb135a3e18e502449
Source dataset
uspto-grants-1994_04
Patent number
US05302712

Reaction notes

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