Hydrochloric Acid → 3-Fluoro-4-(hexadecylamino)benzoic acid

HRID 1389077Notes

Reaction equation

HRID 1389077 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:7]([O:9]CC)=[O:8].C(O)C.Cl>O>[F:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20536470Ethyl 3-fluoro-4-(hexadecylamino)benzoate

Product 1

HCID 205364103-Fluoro-4-(hexadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3.8 g of potassium hydroxide in 15 ml of water is added to a mixture of 3.5 g of ethyl 3-fluoro-4-hexadecylaminobenzoate, 30 ml of water and 30 ml of ethanol. Upon heating, a clear solution is formed and after 20 hours, the hot solution is acidified with concentrated hydrochloric acid and cooled. The precipitate is collected and recrystallized from ethanol and then from chloroform to yield 3-fluoro-4-(hexadecylamino)benzoic acid as a colorless solid.

Workup

  1. temperatureUpon heating
  2. customa clear solution is formed and after 20 hours
  3. temperaturecooled
  4. customThe precipitate is collected
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0a2ad3191c054eb68b80a13be2dee608
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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