Sodium Hydroxide → HCID 15591372, compound

HRID 1633148Notes

Reaction equation

HRID 1633148 reaction equation
BrBr.[OH-:3].[Na+].[O:5]=[C:6](C)[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[C:12]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>O>[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[C:12]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 20441658HCID 20441658, compound

Product 1

HCID 15591372HCID 15591372, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (0.344 ml) is added to a solution of 692 mg of sodium hydroxide in 4 ml of water with ice bath cooling. The resulting solution is added to 400 mg of 1-(5-oxohexyl)-3-methyl-2-(3-pyridyl)indole and this mixture is stirred for 2 hours at room temperature. The mixture is washed with ether. The aqueous solution is filtered and acidified to pH 5-6 with 2 N HCl. A crude white solid is collected which melts in the range 108°-120°. TLC (silica gel; methylene chloride/methanol 9:1) separation gives 1-(4-carboxybutyl)-3-methyl-2-(3-pyridyl)indole of Example 5.

Workup

  1. temperaturecooling
  2. washThe mixture is washed with ether
  3. filtrationThe aqueous solution is filtered
  4. customA crude white solid is collected which
  5. custommelts in the range 108°-120°
  6. customTLC (silica gel; methylene chloride/methanol 9:1) separation

Sources & evidence

ORD record
ord-f2d408bb3d9048d1bec52ccc82105521
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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