Methyl Anthranilate → 2-(4-Fluorophenyl)acetic acid

HRID 1620465Notes

Reaction equation

HRID 1620465 reaction equation
C[O:2]C(=O)C1C=CC=CC=1N.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[O:21])=[CH:15][CH:14]=1.O=S(Cl)Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:21])=[O:2])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 8635Methyl AnthranilateHCID 24386Thionyl ChlorideHCID 37449884-Fluorophenylacetyl chloride

Product 1

HCID 98372-(4-Fluorophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

First, 2-amino-benzoic acid methyl ester (1.00 g, 6.61 mmol) was dissolved in purified CH2Cl2, and DMAP (0.04 g, 0.33 mmol) was added thereto at 0° C. Then, the mixture was added to the reaction vessel containing (4-fluorophenyl)-acetyl chloride produced from reaction of (4-fluoro-phenyl)-acetic acid (1.53 g, 9.90 mmol) with SOCl2, and then reacted at normal temperature for 10 hours. After adding cold sodium bicarbonate solution containing ice, the reaction mixture was extracted with CH2Cl2, and then concentrated under reduced pressure to obtain 1.50 g (79%) of the compound 2-[2-(4-fluorophenyl)-acetylamino]-benzoic acid methyl ester as the solid.

Workup

  1. customat 0° C
  2. additionThen, the mixture was added to the reaction vessel

Sources & evidence

ORD record
ord-89a8400243e741919036cc1137ccd56e
Source dataset
uspto-grants-2014_07
Patent number
US08772493B2

Reaction notes

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