Sodium Hydroxide → HCID 293282, compound

HRID 496637Notes

Reaction equation

HRID 496637 reaction equation
[CH2:1]([C:9]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[NH2:19][C:16]1[CH:17]=[CH:18][C:9]([CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[C:10]([CH:15]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22321866HCID 22321866, compound

Product 1

HCID 293282HCID 293282, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound 77(8.5 g), 2N. aqueous sodium hydroxide (50 ml) and methanol (100 ml) was stirred at ambient temperature for 18 hours and then heated at reflux for 2 hours. The mixture was cooled and evaporated under reduced pressure. The product was redissolved in water (1 L) and washed with diethyl ether (250 ml). The aqueous solution was acidified to pH 5-6 with glacial acetic acid . The resulting precipitate was isolated by filtration and dried under vacuum at 60° C. to give a powder which was azeotroped with toluene (3×50 ml) and then dried under high vacuum to give 5-amino-2-phenethylbenzoic acid (compound 78) (8.0 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under reduced pressure
  5. dissolutionThe product was redissolved in water (1 L)
  6. washwashed with diethyl ether (250 ml)
  7. customThe resulting precipitate was isolated by filtration
  8. customdried under vacuum at 60° C.
  9. customto give a powder which
  10. customwas azeotroped with toluene (3×50 ml)
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-48980af51ea74fc491f6c889b07990fb
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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