HCID 15591375, compound → HCID 13362104, compound

HRID 1633126Notes

Reaction equation

HRID 1633126 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=2)[C:11]([CH3:20])=[C:10]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([OH:3])=[O:2]>Br>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[C:11]([CH3:20])=[C:10]1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 15591375HCID 15591375, compound

Product 1

HCID 13362104HCID 13362104, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1.70 g of 1-(5-carboxypentyl)-5-methoxy-3-methyl-2-(3-pyridyl)indole in 85 ml of 48% hydrobromic acid is heated under reflux for 0.5 hour. The reaction mixture is evaporated to dryness, diluted with water and adjusted to pH 6 with dilute sodium hydroxide. The precipitate is collected and recrystallized from acetone-ether to yield 1-(5-carboxypentyl)5-hydroxy-3-methyl-2-(3-pyridyl)indole.

Workup

  1. temperatureunder reflux for 0.5 hour
  2. customThe reaction mixture is evaporated to dryness
  3. additiondiluted with water
  4. customThe precipitate is collected
  5. customrecrystallized from acetone-ether

Sources & evidence

ORD record
ord-441be0b3e134414698d438dfc541fbde
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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