Hydrochloric Acid → Zofran

HRID 2112270Notes

Reaction equation

HRID 2112270 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH:11]([CH2:15][N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[CH3:21])[C:10](=[O:22])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[ClH:23]>C(O)C.O>[OH2:22].[OH2:22].[ClH:23].[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH:11]([CH2:15][N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[CH3:21])[C:10](=[O:22])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4595Ondansetron

Product 1

HCID 59774ZofranYield 266.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

29.4 g of 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H- carbazol-4-one obtained in Example 9 was suspended in 300 ml of ethanol and 14 ml of water, which was then cooled at −10° C. 12.5 g of conc. HCl was slowly added to the reaction mixture, which was then stirred at room temperature for 2 hours. The resulting solid was filtered and washed with cold ethanol, and then dried in vacuous at 35° C. to give 32.6 g of title compound (yield 90%).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with cold ethanol
  3. customdried in vacuous at 35° C.

Sources & evidence

ORD record
ord-d13e9fbdd36c4ba9b334f4bb9285a049
Source dataset
uspto-grants-2009_04
Patent number
US07521565B2

Reaction notes

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