5-Amino-2-chlorobenzoic acid → HCID 1252891, compound

HRID 713689Notes

Reaction equation

HRID 713689 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].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>O1CCCC1>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:17]([C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)=[O:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 682422-Furancarbonyl chloride

Product 1

HCID 1252891HCID 1252891, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-amino-2-chlorobenzoic acid (13.7 g, 79.85 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) was added furan-2-carbonyl chloride (11.5 g, 88.10 mmol, 1.10 equiv) in a bath of ice and stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and diluted with DCM. The solid was collected by filtration to give 17 g (80%) of 2-chloro-5-(furan-2-amido)benzoic acid as a gray solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with DCM
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-adf99f46c3914c3ba8bc00993ca57295
Source dataset
uspto-grants-2015_11
Patent number
US09186361B2

Reaction notes

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