4-Hydrazinobenzoic acid → Deferasirox

HRID 1401044Notes

Reaction equation

HRID 1401044 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]>CO>[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

4

Reactant 2

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

Product 1

HCID 214348DeferasiroxYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of methanol (450.0 ml), 2-(2-hydroxyphenyl)-benz[1,3]oxazin-4-one (30.0 gm) were stir for 10 min at 25-30° C. To the above contents 4-hydrazino benzoic acid (20.03 gm) was added. The contents were heated to reflux temperature 65-70° C. The contents were maintained for 4 hours at 65-70° C. The reaction mass was cooled Slowly to 0-5° C. and maintained it for 1 hour at 0-5° C. The reaction mass was filtered and washed with methanol (30.0 ml). Compound was taken into methylene chloride and stir for 10 min 25-30° C. The contents were heated to reflux temperature (40-45° C.) and maintained the contents for 1 hr at reflux temperature. Cool the contents to 25-30° C. and stirred for 1 hr at 25-30° C. The reaction mass was filtered and washed with methylene chloride (30.0 ml). Dried the compound at 60-65° C. Yield: 79.0%.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux temperature 65-70° C
  3. temperatureThe contents were maintained for 4 hours at 65-70° C
  4. temperatureThe reaction mass was cooled Slowly to 0-5° C.
  5. temperaturemaintained it for 1 hour at 0-5° C
  6. filtrationThe reaction mass was filtered
  7. washwashed with methanol (30.0 ml)
  8. stirringstir for 10 min 25-30° C
  9. temperatureThe contents were heated
  10. temperatureto reflux temperature (40-45° C.)
  11. temperaturemaintained the contents for 1 hr
  12. temperatureat reflux temperature
  13. temperatureCool the contents to 25-30° C.
  14. stirringstirred for 1 hr at 25-30° C
  15. filtrationThe reaction mass was filtered
  16. washwashed with methylene chloride (30.0 ml)
  17. customDried the compound at 60-65° C

Sources & evidence

ORD record
ord-d759662232c248b58df24119fecbdd49
Source dataset
uspto-grants-2014_12
Patent number
US08907083B2

Reaction notes

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