Hydrochloric Acid → Zofran

HRID 1651605Notes

Reaction equation

HRID 1651605 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 recrystallized 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 recrystallized from a mixture of water (6 ml) and isopropanol (10 ml)

Sources & evidence

ORD record
ord-503feff84eb74749a91ed627a99b26b7
Source dataset
uspto-grants-1990_05
Patent number
US04929632

Reaction notes

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