Hydrochloric Acid → Zofran

HRID 374742Notes

Reaction equation

HRID 374742 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 2° 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°-179.5°.

Workup

  1. filtrationThe hot mixture was filtered
  2. additionthe filtrate diluted with isopropanol (90 ml)
  3. temperaturecooled to 2°
  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-be613548ac2b4b6eaa75364593c4f489
Source dataset
uspto-grants-1996_01
Patent number
US05482716

Reaction notes

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