Hydrochloric Acid → 4-(benzylamino)benzoic acid

HRID 2052483Notes

Reaction equation

HRID 2052483 reaction equation
[CH2:1]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.[OH-].[K+].Cl>O>[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 3832836Ethyl 4-(benzylamino)benzoateHCID 19096565Water ethanol

Product 1

HCID 8535464-(benzylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g. of ethyl p-benzylaminobenzoate (prepared as described in Example 9), 100 ml. of ethanol-water (9:1) and 6.0 g. of potassium hydroxide are refluxed for 3.5 hours. The mixture is acidified with concentrated hydrochloric acid, diluted with water, chilled, filtered and the solid washed with water to give pale cream crystals, m.p. 165°-168° C. Recrystallization from ethanol gives tan crystals, m.p. 167°-169° C.

Workup

  1. additionA mixture of 6.0 g
  2. temperaturechilled
  3. filtrationfiltered
  4. washthe solid washed with water
  5. customto give pale cream crystals, m.p. 165°-168° C
  6. customRecrystallization from ethanol
  7. customgives tan crystals, m.p. 167°-169° C.

Sources & evidence

ORD record
ord-a142c9540a59429a84ed47ac7389c295
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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