Hydrazine hydrate (1:1) → HCID 42610322, compound

HRID 2384536Notes

Reaction equation

HRID 2384536 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:27]3[CH:28]=[N:29][C:30]4[C:35]([CH:36]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:11]([N:15](C(=O)C)[C:16](=[O:18])[CH3:17])[O:12]2)=[CH:7][CH:6]=1)(=O)C.O.NN>C(O)C>[C:16]([NH:15][C:11]1[O:12][C:13]2[C:8]([CH:9]([C:27]3[CH:28]=[N:29][C:30]4[C:35]([CH:36]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:10]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:7][CH:6]=[C:5]([OH:4])[CH:14]=2)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 66866741HCID 66866741, compound

Product 1

HCID 42610322HCID 42610322, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-(acetyloxy)-2-(diacetylamino)-4-quinolin-3-yl-4H-chromene-3-carboxylate (268 mg, 0.55 mmol) was dissolved in absolute ethanol (1.7 mL). Hydrazine hydrate (35 μL, 0.72 mmol) was added and the mixture stirred at room temperature for 1 h. The reaction mixture was evaporated to dryness. 1H NMR analysis showed incomplete conversion of the starting material. The product was suspended in absolute ethanol (1.7 mL) and hydrazine hydrate (35 μL, 0.72 mmol) added. The mixture was stirred at room temperature for 2 h. The mixture was filtered. The residue was washed with ethanol (1.0 mL) and ethyl acetate (2.0 mL). The residue was dissolved in boiling ethanol (16 mL) and the volume reduced to half by heating under a stream of nitrogen. The mixture was cooled to 4° C. and filtered. The residue was dried at the pump to give the title compound (65 mg, 29% yield) as pale yellow needles.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationThe mixture was filtered
  4. washThe residue was washed with ethanol (1.0 mL) and ethyl acetate (2.0 mL)
  5. dissolutionThe residue was dissolved
  6. temperatureby heating under a stream of nitrogen
  7. temperatureThe mixture was cooled to 4° C.
  8. filtrationfiltered
  9. customThe residue was dried at the pump

Sources & evidence

ORD record
ord-5076180eb6a24697ae22afb7880a7b4a
Source dataset
uspto-grants-2012_09
Patent number
US08263775B2

Reaction notes

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