Sodium borohydride → 2-Methyl-1-(4-methoxyphenylmethyl)-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-ol

HRID 324471

Reaction equation

HRID 324471 reaction equation
[CH3:1][C:2]1[N:3]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:5]=2[N:6]=1.[BH4-].[Na+]>C(O)C.ClCCl>[CH3:1][C:2]1[N:3]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([OH:16])[C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220035922-Methyl-1-(4-methoxyphenylmethyl)-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-one

Product 1

HCID 220036712-Methyl-1-(4-methoxyphenylmethyl)-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from step (ii) (1 g) in ethanol (40 ml) and dichloromethane (20 ml) was added sodium borohydride (0.28 g). After 48 h the solvent was evaporated (without heat) under reduced pressure and the residue partitioned between dilute aqueous sodium hydroxide solution and dichloromethane. The organic phase was collected, dried, (MgSO4) and solvent evaporated under reduced pressure to leave a yellow foam.

Workup

  1. customAfter 48 h the solvent was evaporated
  2. temperature(without heat) under reduced pressure
  3. customthe residue partitioned between dilute aqueous sodium hydroxide solution and dichloromethane
  4. customThe organic phase was collected
  5. customdried
  6. custom(MgSO4) and solvent evaporated under reduced pressure
  7. customto leave a yellow foam

Sources & evidence

ORD record
ord-f0b92ae2425049559f19ac78d71468d8
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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