Methylhydrazine → HCID 66958301, compound

HRID 2283789Notes

Reaction equation

HRID 2283789 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-d8cf4f48dc67422799ebef787804f279
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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