Hydrochloric Acid → 2-Fluoro-4-(hexadecylamino)benzoic acid

HRID 1389073Notes

Reaction equation

HRID 1389073 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].C(O)C.[OH-].[K+].Cl>O>[F:1][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20536430Methyl 2-fluoro-4-hexadecylaminobenzoate

Product 1

HCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g of methyl 2-fluoro-4-hexadecylaminobenzoate, 40 ml of ethanol, 60 ml of water, and 3.8 g of potassium hydroxide is heated on a steam bath for 14 hours. The hot solution is acidified with concentrated hydrochloric acid. The reaction mixture is cooled and filtered. The colorless residue is recrystallized from chloroform-hexane to yield 2-fluoro-4-(hexadecylamino)benzoic acid as a white solid.

Workup

  1. temperatureis heated on a steam bath for 14 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customThe colorless residue is recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-1f71faaefca647619ad18acb3f513e20
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

Loading…