Hydrochloric Acid → Zofran

HRID 1264454Notes

Reaction equation

HRID 1264454 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.C([OH:26])(C)C.[ClH:27]>O>[OH2:22].[OH2:26].[ClH:27].[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 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 4595Ondansetron

Product 1

HCID 59774Zofran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one (18.3 g) in a hot mixture of isopropanol (90 ml) and water (18.3 ml) was treated with concentrated hydrochloric acid (6.25 ml). The hot mixture was filtered and the filtrate diluted with isopropanol (90 ml) and stirred at room temperature for 17 h, cooled to 20 and the solid filtered off (21.6 g). A sample (6 g) was recrystallised from a mixture of water (6 ml) and isopropanol (10 ml) to give the title compound as a white crystalline solid (6 g) m.p. 178.5-179.50.

Workup

  1. filtrationThe hot mixture was filtered
  2. additionthe filtrate diluted with isopropanol (90 ml)
  3. temperaturecooled to 20
  4. filtrationthe solid filtered off (21.6 g)
  5. customA sample (6 g) was recrystallised from a mixture of water (6 ml) and isopropanol (10 ml)

Sources & evidence

ORD record
ord-ffd335555ade4c15a3fc512680e380c1
Source dataset
uspto-grants-2003_04
Patent number
US06544550B1

Reaction notes

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