Citric Acid → HCID 58508945, compound

HRID 454568Notes

Reaction equation

[OH-].[Na+].C([O:6][C:7]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[C:20]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:10])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[O:24]1[CH:25]=[CH:26][C:22]([C:20]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:27]=[C:28]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH:29]=[CH:30][C:7]=3[OH:6])[CH:21]=2)=[CH:23]1

Participants

Conditions

Temperature: 52.5 °C

Procedure

Dioxane (5.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.31 mL) were added to the obtained methyl 2-(2-acetoxy-5-(pyridin-3-yl)benzamido)-4-(furan-3-yl)benzoate (0.11 g), followed by stirring at 50 to 55° C. for 1 hours. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid (6 mL) was added thereto. The solid substance was collected by filtration to obtain 0.081 g of 4-(furan-3-yl)-2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-benzoic acid as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record: ord-98398badb503465ebede7018fd87ec0c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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