Hydrazine hydrate (1:1) → HCID 135519368, compound

HRID 1867567Notes

Reaction equation

HRID 1867567 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([C:13]([OH:15])=[O:14])=[C:6]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:5]2=O.O.[NH2:26][NH2:27]>C(O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[C:6]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:7]([C:13]([OH:15])=[O:14])[NH:26][N:27]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11416722HCID 11416722, compound

Product 1

HCID 135519368HCID 135519368, compound

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6-Chloro-7-hydroxy-3-(4methoxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid (1 eq) was taken up in ethanol and hydrazine hydrate (3 eq) was added. To aid dissolution a few drops of NaHCO3 (aq) was added, and then all was heated at 70° C. under nitrogen for 2 hours. The solution was cooled to room temperature and concentrated in vacuo to a brown oil. This was partitioned between 1MHCl(aq) and diethyl ether. The organic phases were combined, washed with 1MHCl(aq), dried over MgSO4, filtered and concentrated in vacuo to give 5-(5-chloro-2,4dihydroxy-phenyl)-4-(4-methoxy-phenyl)-2H-pyrazole-3-carboxylic acid as a yellow foam.

Workup

  1. additionwas added
  2. temperatureThe solution was cooled to room temperature
  3. concentrationconcentrated in vacuo to a brown oil
  4. customThis was partitioned between 1MHCl(aq) and diethyl ether
  5. washwashed with 1MHCl(aq)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e28302da3592433696f6ec7d8b64caf9
Source dataset
uspto-grants-2009_12
Patent number
US07632855B2

Reaction notes

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