Bromine → HCID 18988172, compound

HRID 2396013Notes

Reaction equation

HRID 2396013 reaction equation
[Br:1]Br.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([N:11]1[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]1=[O:21])[CH2:4]2>C(O)(=O)C>[N:3]12[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]1)[CH:5]([N:11]1[CH:20]=[C:19]([Br:1])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]1=[O:21])[CH2:4]2

Participants

4

Reactant 2

HCID 24408BromineHCID 15656869HCID 15656869, compound

Product 1

HCID 18988172HCID 18988172, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of Br2 (1.0M) in glacial acetic acid (0.8 mL) was added to a solution of (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-l(2H)-isoquinolinone (0.20 g; 0.787 mmol), from Example 2, in glacial acetic acid (5.0 mL). Thesolvent was removed under pressure and the residue was partitioned between methylene chloride (100 ml) and sodium carbonate (2.0M, 30 ml). The organic phase was separated and dried over anhydrous sodium sulfate. The mixture was then filtered and concentrated under reduced pressure. The solid residue was dissolved in ethyl alcohol (2 ml) and the solution acidified with hydrochloric acid (10%). A small amount of ethyl ether was added and crystals were collected and dried in vacuo to give (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-4-bromo-1(2H)-isoquinolinone (0.0832 g, 0.248 mmol), m.p. 208°-209° C.

Workup

  1. customThesolvent was removed under pressure
  2. customthe residue was partitioned between methylene chloride (100 ml) and sodium carbonate (2.0M, 30 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe solid residue was dissolved in ethyl alcohol (2 ml)
  8. additionA small amount of ethyl ether was added
  9. customcrystals were collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-65d48b9ff7c54886b448ee80da686233
Source dataset
uspto-grants-1996_02
Patent number
US05491148

Reaction notes

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