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

HRID 1296956Notes

Reaction equation

HRID 1296956 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-(4-methoxy-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 1M HCl (aq) and diethyl ether. The organic phases were combined, washed with 1M HCl (aq), dried over MgSO4, filtered and concentrated in vacuo to give 5-(5-chloro-2,4-dihydroxy-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 1M HCl (aq) and diethyl ether
  5. washwashed with 1M HCl (aq)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98a05657a50a4ebb8193f511c258c0f6
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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