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

HRID 1389111Notes

Reaction equation

HRID 1389111 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:5]=[CH:4][C:3]=1[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[K+].C(O)C.O.Cl>O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:5]=[CH:4][C:3]=1[CH2:25][C:26]([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 54400635Ethyl 2-fluoro-4-(hexadecylamino)phenylacetate

Product 1

HCID 538935342-Fluoro-4-(hexadecylamino)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g. of ethyl 2-fluoro-4-(hexadecylamino)phenylacetate, 7.0 g. of potassium hydroxide and 100 ml. of ethanol-water is heated to reflux for 4 hours. While hot, the mixture is adjusted to pH 7 with conc. hydrochloric acid. The mixture is diluted with water, cooled and filtered. Recrystallization of the precipitate yields 2-fluoro-4-(hexadecylamino)phenylacetic acid.

Workup

  1. additionA mixture of 6.0 g
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customRecrystallization of the precipitate

Sources & evidence

ORD record
ord-67974d0a243a4238a69d739ee7a4551c
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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