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

HRID 1156101Notes

Reaction equation

HRID 1156101 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-8a72b49723cd4fbfb106c2202db60105
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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