Potassium Carbonate → 2-(3-Hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 2405210Notes

Reaction equation

HRID 2405210 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24]C(=O)C)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 670765742-(3-Acetoxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

Product 1

HCID 670765182-(3-Hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl esterYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of step 1 (3.44 g, 8.97 mmol) was dissolved in methanol (50 ml), potassium carbonate (248 mg, 1.79 mmol) was added and the mixture was stirred for 2 h at room temperature. The mixture was evaporated to dryness, the residue partitioned between EA and 1 N hydrochloric acid and the aqueous phase extracted with EA. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated to dryness to give 2.80 g of the title compound.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between EA and 1 N hydrochloric acid
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-68d86fd6f15b44dc9fe365953b73d567
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

Loading…