4-Aminobenzoic Acid → HCID 16228385, compound

HRID 1499369Notes

Reaction equation

HRID 1499369 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH:11]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCOCC1>[CH:11]1([C:16]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 78284Cyclopentanecarbonyl chloride

Product 1

HCID 16228385HCID 16228385, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 1 liter 2-neck roundbottom flask, 40 grams of 4-aminobenzoic acid was dissolved in about 400 mL of dioxane. Then, 19.35 g of cyclopentanecarbonyl chloride was added dropwise to the solution. The reaction intermediate, 4-(cyclopentanecarbonyl-amino)-benzoic acid, formed as a white solid in the step and was collected by filtration. After washing the product with about 200 mL dioxane and then with about 1 liter of boiling water, the reaction intermediate was dried in an oven at 110° C. The yield at this step was about 27.7 g (81%).

Sources & evidence

ORD record
ord-0bafa64e13664adc9a8236dfbf3c1087
Source dataset
uspto-grants-2015_12
Patent number
US09200142B2

Reaction notes

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