Phenylhydrazine → HCID 178515132, compound

HRID 323626Notes

Reaction equation

HRID 323626 reaction equation
CO[C:3]([C:5]1[C:14]([C:15]([O:17]C)=O)=[C:13]([OH:19])[C:12]2[C:7](=[CH:8][C:9]([Cl:21])=[CH:10][C:11]=2[Cl:20])[N:6]=1)=[O:4].[C:22]1([NH:28][NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[Cl:21][C:9]1[CH:10]=[C:11]([Cl:20])[C:12]2[C:13](=[O:19])[C:14]3[C:15](=[O:17])[N:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:29]=[C:3]([OH:4])[C:5]=3[NH:6][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 178418430HCID 178418430, compound

Product 1

HCID 178515132HCID 178515132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl-5,7-dichloro-4-hydroxyquinoline-2,3-dicarboxylate (3.00 g, 9.09 mM) in ethanol (42 mL) was added phenylhydrazine (6.26 mL, 63.6 mM). The resulting green solution was heated to reflux for 16 hours during which time a small amount of red precipitate formed. This suspension was cooled to room temperature with stirring and additional precipitation occurred to give a thick tan suspension. The solids were collected and washed with ethanol (the ethanol washes were saved). The collected solids were recrystallized from ethanol (1.20 L) to give the phenylhydrazine salt of the title compound (1.17 g) as a tan powder. This material was stirred and refluxed in glacial acetic acid (15 mL) for 2.5 hours and then cooled to room temperature with stirring. The resulting orange suspension was filtered to give the title compound (0.629 g, 19%) as an orange powder which was slightly impure. An analytical sample of the title compound was obtained from the above saved ethanol washes by filtration of a precipitate which formed after these washes stood for several hours. Recrystallization of this collected tan powder (0.126 g) from glacial acetic acid (2 mL) gave the pure title compound (0.083 g) as an orange powder, mp 364-367° C.; MS(CI): 374 (M+H).

Workup

  1. temperatureThe resulting green solution was heated
  2. temperatureto reflux for 16 hours during which time a small amount of red precipitate
  3. customformed
  4. customadditional precipitation
  5. customto give a thick tan suspension
  6. customThe solids were collected
  7. washwashed with ethanol (the ethanol washes
  8. customThe collected solids were recrystallized from ethanol (1.20 L)

Sources & evidence

ORD record
ord-0e97cc213e5747aa8e7b532cdd5f2636
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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