Sodium Bicarbonate → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(imidazol-1-yl)aniline

HRID 1830418Notes

Reaction equation

HRID 1830418 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:38])[C:5]([CH3:37])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:33]C(=O)C)=[C:17]([CH:32]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:38])[C:5]([CH3:37])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:33])=[C:17]([CH:32]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054178N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(imidazol-1-yl)aniline

Product 1

HCID 22054221N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(imidazol-1-yl)anilineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(imidazol-1-yl)aniline (0.070 g, 0.136 mmol) was dissolved in methanol (5 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (3 ml), the solution was stirred at room temperature for 3 hours. After the completion of reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was recrystallized from ether to obtain the titled compound (0.063 g, 0.133 mmol, 98%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was recrystallized from ether

Sources & evidence

ORD record
ord-4a1914d38ca94f70aa53d1a8672dcb75
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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