Sodium Hydroxide → HCID 18687373, compound

HRID 1872715Notes

Reaction equation

HRID 1872715 reaction equation
C([NH:4][C:5]1[C:24]([Br:25])=[CH:23][C:8]([C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][N:16]([CH3:22])[CH2:17]3)=[O:10])=[C:7]([O:26][CH3:27])[CH:6]=1)(=O)C.[OH-].[Na+]>C(O)C.O>[CH3:22][N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][CH:20]=[CH:21][C:12]=2[NH:11][C:9](=[O:10])[C:8]2[CH:23]=[C:24]([Br:25])[C:5]([NH2:4])=[CH:6][C:7]=2[O:26][CH3:27])[CH2:17]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 186874624-acetylamino-5-bromo-2-methoxy-N-(2-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide

Product 1

HCID 18687373HCID 18687373, compoundYield 7.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-acetylamino-5-bromo-2-methoxy-N-(2-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide (0.888 g, 2 mmol) in ethanol (30 ml) and water (10 ml) was added 10% aqueous sodium hydroxide (1.25 ml). The mixture was heated at reflux for 1.25h before pouring into water and extracting with chloroform. The organic layer was dried over sodium sulfate, concentrated in vacuo and the residue recrystallised from ethyl acethate to afford the title compound as a brown solid (0.062 g).

Workup

  1. temperatureThe mixture was heated
  2. extractionextracting with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue recrystallised from ethyl acethate

Sources & evidence

ORD record
ord-ec215de01b8d45da83569ec45b2a897e
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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