Sodium Bicarbonate → 5-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid

HRID 637681Notes

Reaction equation

HRID 637681 reaction equation
[Cl:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([O:12]C)=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.C(=O)(O)[O-].[Na+]>Br.O>[Cl:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([OH:12])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 541834705-Chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid

Product 1

HCID 539130445-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 8.5 g (30 mmole) of 5-chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid in 150 ml of 48% hydrobromic acid is boiled under reflux for 15 hours. The reaction mixture is cooled, diluted with water and adjusted to pH 3-4 with saturated sodium bicarbonate solution. The whole is subsequently extracted with ethyl acetate and the combined organic phases are washed with water, dried over sodium sulphate and concentrated by evaporation in a vacuum rotary evaporator. In that manner a dark grey foam of 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid is obtained which is reacted, without purification, to form 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one.

Workup

  1. temperatureunder reflux for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionThe whole is subsequently extracted with ethyl acetate
  4. washthe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation in a vacuum rotary evaporator

Sources & evidence

ORD record
ord-7452b70b0ab14af28daffa3c840e9f0b
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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