Hydrazine hydrate (1:1) → HCID 20096580, compound

HRID 2221110Notes

Reaction equation

HRID 2221110 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])[CH3:2].O.NN>COCCOC>[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20096586HCID 20096586, compound

Product 1

HCID 20096580HCID 20096580, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1,2-Dimethoxyethane (1.0 L) is added to (2-nitro4-phtalimido-phenyl)-carbamic acid ethyl ester (101 g, 0.28 mol) and the mixture is heated under reflux. Hydrazine monohydrate (19.6 g, 0.39 mol) is added dropwise over 10 minutes and the mixture is stirred at reflux for 1.5 hours. Upon cooling to ambient temperature the mixture is filtered and the solids are washed with dimethoxyethane (250 mL) on the filter. The filtrate is concentrated by means of evaporation and the red crystalline product is recrystallized from toluene (350 mL), precipitated product is filtered off and dried in vacuo. The mother liquor is concentrated to half the original volume and left standing for 16 hours. Precipitated material is filtered off and recrystallized as before. The recrystallized solids are combined to furnish a total of 57.6 g (90%) dark red title compound. LC/MS (m/z) 225.1 (MH+); tR=2.08 min. 1H NMR (CDCl3): 1.33 (t, 3H); 3.77 (s, 2H, NH2); 4.23 (q, 2H); 6.98 (dd, 1H); 7.45 (d, 1H); 8.28 (d, 1H); 9.39 (s, 1H, NH).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureat reflux for 1.5 hours
  4. filtrationis filtered
  5. washthe solids are washed with dimethoxyethane (250 mL) on the filter
  6. concentrationThe filtrate is concentrated by means of evaporation
  7. customthe red crystalline product is recrystallized from toluene (350 mL)
  8. customprecipitated product
  9. filtrationis filtered off
  10. customdried in vacuo
  11. concentrationThe mother liquor is concentrated to half the original volume
  12. waitleft
  13. filtrationPrecipitated material is filtered off
  14. customrecrystallized as before

Sources & evidence

ORD record
ord-a51d9804279f43c594fe32c28cb5dc6c
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

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