Methyl 4-Amino-2-chlorobenzoate → HCID 67395110, compound

HRID 1023721Notes

Reaction equation

HRID 1023721 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>>[Cl:15][C:16]1[CH:25]=[C:24]([NH:26][C:12]([C:6]2[O:7][C:8]([CH:9]([CH3:10])[CH3:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[O:14])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

3

Reactant 2

HCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 584205144,5-Diisopropylfuran-2-carboxylic acid

Product 1

HCID 67395110HCID 67395110, compoundYield 72%

Procedure

In the same manner as that of Example 24, 4,5-diisopropylfuran-2-carboxylic acid (80 mg, 0.408 mmol) and methyl 2-chloro-4-aminobenzoate (136 mg, 0.733 mmol) were condensed, the reaction mixture was treated in a conventional manner, and then the residue was purified by silica gel chromatography [hexane-ethyl acetate (40:1)] and recrystallized to obtain methyl 2-chloro-4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoate (106 mg, 72%) as colorless prisms.

Workup

  1. customcondensed
  2. additionthe reaction mixture was treated in a conventional manner
  3. customthe residue was purified by silica gel chromatography [hexane-ethyl acetate (40:1)]
  4. customrecrystallized

Sources & evidence

ORD record
ord-49b40a0b2c4f4b7b85c526adedd69901
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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