Sodium Hydroxide → HCID 57435135, compound

HRID 1724807Notes

Reaction equation

HRID 1724807 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:21])=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+]>CCO>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=2[CH3:21])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435136HCID 57435136, compound

Product 1

HCID 57435135HCID 57435135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[2-(3-methoxy-phenyl)-ethyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (127) in EtOH, 3 equiv of NaOH aq (3 M) was added then the mixture was heated at 80° C. for 1 hour. When the reaction is judged complete, the solvent was removed under vacuum, H2O was added and an equal volume of Et2O was added. The organic layer was removed then the aqueous layer was made acidic with HCl (1M). If the product precipitated out at this point, it was filtered off, washed with H2O, and dried to obtain pure desired product. If the product didn't crash out when the aqueous layer is made acidic, Et2O was added, and the organic layer was removed (2×). The organic layer was dried with Na2SO4, filtered, and concentrated to obtain desired product. Purification: Extraction. Amount: 37 mg. 1H (CDCl3, 400 MHz): δ 8.90 (NH, broad s), 7.19 (1H, dd), 6.88 (1H, s), 6.75 (2H, m), 6.94 (1H, s), 3.78 (3H, s), 2.80 (2H, dd), 2.68 (2H, dd), 2.08 (3H, s) ppm. 13C (CDCl3, 100 MHz): δ 165.5, 159.6, 143.5, 132.3, 129.3, 122.6, 121.0, 118.7, 117.8, 114.2, 111.2, 55.2, 37.3, 27.8, 11.3 ppm. HPLC (20 min): 91.6%. LC/MS: 97%.

Workup

  1. customthe solvent was removed under vacuum, H2O
  2. additionwas added
  3. additionan equal volume of Et2O was added
  4. customThe organic layer was removed
  5. customIf the product precipitated out at this point, it
  6. filtrationwas filtered off
  7. washwashed with H2O
  8. customdried

Sources & evidence

ORD record
ord-b532af4b096d415b92147975c60a9d1b
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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