4-Hydrazinobenzoic acid → Deferasirox

HRID 1092191Notes

Reaction equation

HRID 1092191 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=O)[N:13]=1.[NH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[NH2:20]>C(OCC)(=O)C.C(O)(=O)CC>[CH:16]1[CH:17]=[CH:18][C:10]([OH:9])=[C:11]([C:12]2[N:13]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[N:20]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 214348DeferasiroxYield 84.4%

Reagents, catalysts & solvents 2

HCID 1032Propionic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
92 °C

Procedure

A suspension of 0.7 g (2.92 mmol) of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one and 0.52 g (3.44 mmol) of 4-hydrazinobenzoic acid in 8 ml ethyl acetate and 5.0 ml of propionic acid is heated to its boiling point and maintained at this temperature (92° C.) for 2 hours. After completion of the reaction, the mixture is cooled and filtered. The product is washed with ethyl acetate. After drying, 0.92 g of raw deferasirox is obtained, i.e. 84% of the theory, with an HPLC purity of 99.7% and a melting temperature of 258 to 263° C.

Workup

  1. temperatureis heated to its boiling point
  2. customAfter completion of the reaction
  3. temperaturethe mixture is cooled
  4. filtrationfiltered
  5. washThe product is washed with ethyl acetate
  6. customAfter drying

Sources & evidence

ORD record
ord-b1ba798f6c95492ba1f238bce8cc4821
Source dataset
uspto-grants-2012_03
Patent number
US08129421B2

Reaction notes

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