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

HRID 324483
Notes
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Reaction equation

HRID 324483 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16](=[O:17])[C:10]3[N:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.[BH4-].[Na+]>C(O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([OH:17])[C:10]3[N:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220035787-Chloro-1,2-dimethyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-one

Product 1

HCID 22003588(+/-)-7-Chloro-1,2-dimethyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the product from step (ii) (1.43 g), and sodium borohydride (0.42 g) in ethanol (100 ml) and dichloromethane (20 ml) were heated at 50° C. for 4 h. The solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane, washed with dilute aqueous sodium hydroxide solution, dried (CaCl2), and evaporated to give the subtitled product as a brown solid.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with dilute aqueous sodium hydroxide solution
  4. dry with materialdried (CaCl2)
  5. customevaporated

Sources & evidence

ORD record
ord-680b5f8b98954f02be172cf03af1e864
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06218376B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes