Hydrochloric Acid → 4-({2-[4-(Benzyloxy)phenyl]ethyl}amino)benzoic acid

HRID 1703083Notes

Reaction equation

HRID 1703083 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][CH2:14][NH:15][C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.O.Cl>O>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][CH2:14][NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079675Ethyl 4-({2-[4-(benzyloxy)phenyl]ethyl}amino)benzoateHCID 19096565Water ethanol

Product 1

HCID 130796744-({2-[4-(Benzyloxy)phenyl]ethyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g. of ethyl p-[(p-benzyloxyphenethyl)amino]benzoate (prepared as described in Example 18) 6.0 g. of potassium hydroxide and 100 ml. of ethanol-water (9:1) is refluxed for 3.5 hours. The mixture is acidified while hot with concentrated hydrochloric acid, diluted with water, filtered and the solid washed with water to give tan crystals, m.p. 180°-185° C. Recrystallization from glacial acetic acid gives tan crystals, m.p. 187°-189° C.

Workup

  1. additionA mixture of 6.0 g
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customto give tan crystals, m.p. 180°-185° C
  5. customRecrystallization from glacial acetic acid
  6. customgives tan crystals, m.p. 187°-189° C.

Sources & evidence

ORD record
ord-8dcd6d600eb045b6967102814775c0eb
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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