Hydrazine hydrate (1:1) → 1110650-72-0

HRID 2384535Notes

Reaction equation

HRID 2384535 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[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(OCC)(=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][CH:30]=[CH:31][CH:32]=3)[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

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66868270HCID 66868270, compound

Product 1

HCID 426015121110650-72-0Yield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(acetyloxy)-2-(diacetylamino)-4-pyridin-3-yl-4H-chromene-3-carboxylate (6.989 g, 15.9 mmol) was dissolved in absolute ethanol (50 mL). Hydrazine hydrate (950 μL, 19.5 mmol) was added and the mixture stirred at room temperature for 6 h. The reaction mixture was evaporated to dryness to give an orange solid. The residue was dissolved in a mixture of ethyl acetate (200 mL) and ethanol (50 mL). Silica gel 60 (35 g) was added and the mixture evaporated to dryness. Purified by flash chromatography over silica gel 60, 40-63 μm (eluent: 75% ethyl acetate/petroleum spirits (54×100 mL fractions), packing height: 15 cm, column diameter: 5 cm). The fractions containing the major band (Rf 0.26, eluent: 75% ethyl acetate/petroleum spirits, fractions 15-53) were combined and evaporated to dryness to give the title compound (3.307 g, 59% yield) as a pale yellow powder.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customto give an orange solid
  3. additionSilica gel 60 (35 g) was added
  4. customthe mixture evaporated to dryness
  5. customPurified by flash chromatography over silica gel 60, 40-63 μm (eluent: 75% ethyl acetate/petroleum spirits (54×100 mL fractions), packing height: 15 cm, column diameter: 5 cm)
  6. additionThe fractions containing the major band (Rf 0.26, eluent: 75% ethyl acetate/petroleum spirits, fractions 15-53)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-476fbf1761bd47e88675bed92eb60166
Source dataset
uspto-grants-2012_09
Patent number
US08263775B2

Reaction notes

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