Hydrazine → HCID 14257799, compound

HRID 868259Notes

Reaction equation

HRID 868259 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([C:11](=O)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:7]([CH3:21])[C:6]=2[CH:5]=[C:4]([CH3:22])[C:3]=1[CH3:23].[OH-].[K+].NN>C(O)CO>[OH:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:7]([CH3:21])[C:6]=2[CH:5]=[C:4]([CH3:22])[C:3]=1[CH3:23]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 14257798HCID 14257798, compound

Product 1

HCID 14257799HCID 14257799, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

The crude material from Step 3 was dissolved in ethylene glycol (600 mL) and KOH pellets (125 g) and anhydrous hydrazine (36 mL) were added. The reaction was heated to 150° C. for 2 hr, then cooled to RT (room temperature) and diluted with 10% NH4OAc buffer (1.5 L) and the product was extracted into EtOAc. The crude product was chromatographed on silica gel (5% EtOAc/toluene) to yield the title compound, which was recrystallized in ether/hexane.

Workup

  1. temperaturecooled to RT (room temperature)
  2. extractionthe product was extracted into EtOAc
  3. customThe crude product was chromatographed on silica gel (5% EtOAc/toluene)

Sources & evidence

ORD record
ord-8b4c6c40b30c48209deddafef06122b6
Source dataset
uspto-grants-1988_10
Patent number
US04778805

Reaction notes

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