Methylhydrazine → HCID 66958301, compound

HRID 1984389Notes

Reaction equation

HRID 1984389 reaction equation
O=[C:2]([CH2:8][C:9](=O)[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[CH3:25][NH:26][NH2:27]>C(O)(=O)C>[O:22]=[C:13]1[C:14]2[C:15](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:17])[N:12]1[CH2:11][CH2:10][C:9]1[N:26]([CH3:25])[N:27]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 5360545SodiumHCID 66958840HCID 66958840, compound

Product 1

HCID 66958301HCID 66958301, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A modification of the method described in Part A of Example 11 was followed. A mixture of ethyl 2,4-dioxo-6-phthalimidohexanoate, sodium salt (prepared as described in Part A of Example 23, 100 g, 295 mmol) in glacial acetic acid (0.3 L) was cooled to 9° C. before the addition of methylhydrazine (16.0 mL,300 mmol). During the addition, the reaction temperature did not exceed 16° C. Solids were rinsed from the inside of the flask walls into the mixture with acetic acid (50 mL) and the mixture was allowed to warm to ambient temperature and stir overnight. Water was added to the mixture and additional solid precipitated. The solid was isolated by filtration, dried, and recrystallized from ethanol. The solid was isolated and dried to yield 75.2 g of ethyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-methyl-1H-pyrazole-3-carboxylate.

Workup

  1. customprepared
  2. additionDuring the addition
  3. customdid not exceed 16° C
  4. washSolids were rinsed from the inside of the flask walls into the mixture with acetic acid (50 mL)
  5. additionWater was added to the mixture and additional solid
  6. customprecipitated
  7. customThe solid was isolated by filtration
  8. customdried
  9. customrecrystallized from ethanol
  10. customThe solid was isolated
  11. customdried

Sources & evidence

ORD record
ord-1ec34dc72ac04a4381f5e21747cdeded
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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