Water → 4-Bromo-2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline

HRID 980920Notes

Reaction equation

HRID 980920 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:18])[CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH2:8][CH2:7]2.[Br:19]Br.O.[OH-].[Na+]>C(O)(=O)C>[Br:19][C:5]1[C:4](=[O:18])[NH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 137720565,6,7,8-Tetrahydro-1-methyl-7-(4-pyridinyl)-3(2h)-isoquinolinone

Product 1

HCID 137720644-Bromo-2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinolineYield 39.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2,3,5,6,7,8-Hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline (0.4 g) obtained in Example 1 was dissolved in 6 ml of acetic acid, and a solution of 0.27 g of bromine and 1.3 ml of acetic acid was dropwise added at 45° C. After the reaction was completed, the reaction mixture was poured into water and an aqueous solution of sodium hydroxide was added to adjust the pH to 9-10. The deposit was filtered out and recrystallized from methanol. Thus, there was obtained 0.21 g of 4-bromo-2,3,5,6,7,8-hexahydro-1-methyl-3-oxo-7-(4-pyridyl)isoquinoline.

Workup

  1. filtrationThe deposit was filtered out
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-14604962b81a445b9b0de0a5e622cc54
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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