Hydrochloric Acid → 4-{[3-(2-Methoxyphenyl)propyl]amino}benzoic acid

HRID 1703100Notes

Reaction equation

HRID 1703100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=1.[OH-].[K+].C(O)C.O.Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079682Ethyl 4-{[3-(2-methoxyphenyl)propyl]amino}benzoateHCID 19096565Water ethanol

Product 1

HCID 130796814-{[3-(2-Methoxyphenyl)propyl]amino}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.0 g. of ethyl p-[3-(o-methoxyphenyl)propyl]aminobenzoate (prepared as described in Example 41), 7.0 g. of potassium hydroxide and 100 ml. of ethanol-water (9:1) is refluxed for 3.5 hours, acidified while hot with concentrated hydrochloric acid, diluted with water and chilled. The mixture is filtered and the solid washed with water to give off-white crystals, m.p. 155°-157° C. Recrystallization from ethanol gives off-white crystals, m.p. 156°-158° C.

Workup

  1. additionA mixture of 7.0 g
  2. temperaturechilled
  3. filtrationThe mixture is filtered
  4. washthe solid washed with water
  5. customto give off-white crystals, m.p. 155°-157° C
  6. customRecrystallization from ethanol
  7. customgives off-white crystals, m.p. 156°-158° C.

Sources & evidence

ORD record
ord-db3cbc251dfd4bbc819b3218de6902f4
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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