5-Amino-2-chlorobenzoic acid → 2-Chloro-5-(3-Fluoro-Benzoylamino)-Benzoic Acid

HRID 1662818

Reaction equation

HRID 1662818 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C1COCC1>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([F:12])[CH:14]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 286675042-Chloro-5-(3-Fluoro-Benzoylamino)-Benzoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-chloro-benzoic acid (0.96 g, 5.58 mmol) was diluted with THF (60 mL), treated with 3-fluoro-benzoyl chloride (0.738 mL, 6.14 mmol) and stirred for 18 h. Solvents were then removed and resulting solids were triturated with DCM. After filtration, the title compound was obtained as a white solid (1.7 g, 99%).

Workup

  1. customSolvents were then removed
  2. customresulting solids
  3. customwere triturated with DCM
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-3a0aa06eb6a445f9bbbfcb5858b9c772
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Linked notes

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