Hydrazine hydrate (1:1) → HCID 178418252, compound

HRID 1451304Notes

Reaction equation

HRID 1451304 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:22])=[C:5]([C:18](OC)=[O:19])[C:6]([C:14](OC)=[O:15])=[N:7]2.O.[NH2:24][NH2:25]>C(O)C>[Br:1][C:2]1[C:3]2[C:4]([OH:22])=[C:5]3[C:18](=[O:19])[NH:25][NH:24][C:14](=[O:15])[C:6]3=[N:7][C:8]=2[CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178435441HCID 178435441, compound

Product 1

HCID 178418252HCID 178418252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of dimethyl 5-bromo-7-ethyl-4-hydroxyquinoline -2,3-dicarboxylate (1.0 g, 2.7 mM,) in ethanol (25 mL) was added hydrazine hydrate (0.68 g, 14 mM). The resulting mixture was concentrated at 30° C. using a rotary evaporator and the residue was diluted with another portion of ethanol (25 mL) and similarly concentrated at 30° C. The residue was suspended in ethanol and filtered to separate the title compound (0.82 g, 82%) as a light yellow solid. Recrystallization of a portion of this material from dimethylsulfoxide/ethanol provided an analytical sample of the title compound as a light yellow crystalline solid, mp 335°-340° C. (dec). Analysis for C13H14BrN5O3 ·0.35 H2O Calculated: C, 41.70; H, 3.95; N, 18.70 Found: C, 41.99; H, 3.84; N, 18.31

Workup

  1. concentrationThe resulting mixture was concentrated at 30° C.
  2. customa rotary evaporator
  3. additionthe residue was diluted with another portion of ethanol (25 mL)
  4. concentrationsimilarly concentrated at 30° C
  5. filtrationfiltered
  6. customto separate the title compound (0.82 g, 82%) as a light yellow solid
  7. customRecrystallization of a portion of this material from dimethylsulfoxide/ethanol

Sources & evidence

ORD record
ord-b78b893a7384422eb1036f8404eccbe6
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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