Sodium Bicarbonate → HCID 13424127, compound

HRID 1980851Notes

Reaction equation

HRID 1980851 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:13][C:12]([O:26]C)=[CH:11][CH:10]=3)[CH:2]=1.C(=O)(O)[O-].[Na+]>Br>[OH:26][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13424121HCID 13424121, compound

Product 1

HCID 13424127HCID 13424127, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1.5 g of 2-(3-pyridyl)-3-[5-(ethoxycarbonyl)-pentyl]-5-methoxyindole in 15 ml of 48% hydrobromic acid is treated at reflux temperature for 2.5 hours. The reaction solution is cooled and neutralized with sodium bicarbonate solution to pH 6-7, and then extracted with ethyl acetate. The organic extract is dried (MgSO4), filtered, and concentrated to give a solid which is recrystallized from acetonitrile to give 5-hydroxy-2-(3-pyridyl)-3-(5-carboxypentyl)-indole, m.p. 185°-187°.

Workup

  1. temperatureat reflux temperature for 2.5 hours
  2. temperatureThe reaction solution is cooled
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialis dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid which
  9. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-31a4925953984ed88c21864fe9915ba0
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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