Sodium borohydride → (+/-)-7-Chloro-1-(2-hydroxyethyl)-2-methyl-4h-benzo[5,6]cyclohepta[1,2-d]imidazol-4-ol

HRID 324510Notes

Reaction equation

HRID 324510 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:18](=[O:19])[C:10]3[N:11]=[C:12]([CH3:17])[N:13]([CH2:14][CH2:15][OH:16])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:20]=1.[BH4-].[Na+]>C(O)C.CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:18]([OH:19])[C:10]3[N:11]=[C:12]([CH3:17])[N:13]([CH2:14][CH2:15][OH:16])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220035917-Chloro-1-(2-hydroxyethyl)-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-one

Product 1

HCID 22003582(+/-)-7-Chloro-1-(2-hydroxyethyl)-2-methyl-4h-benzo[5,6]cyclohepta[1,2-d]imidazol-4-ol

Reagents, catalysts & solvents 2

HCID 180AcetoneCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of step (i) (0.79 g) in ethanol (100 ml) was treated with sodium borohydride (0.207 g) followed by heating at reflux for 4 hours. The mixture was treated with a few drops of acetone and then concentrated under reduced pressure to dryness. Used directly in the next step.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 4 hours
  3. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-b66e2b2a9e4341a1a088fc45133d9dea
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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