Methanol → HCID 13519804, compound

HRID 653424Notes

Reaction equation

HRID 653424 reaction equation
COC(=O)[CH:4]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[CH2:14]2)[C:5](OC)=O.[OH-:20].[Na+].[CH3:22][OH:23]>>[O:18]=[C:15]1[CH2:14][C:13]2[C:17](=[C:9]([CH2:4][CH2:5][C:22]([OH:23])=[O:20])[CH:10]=[CH:11][CH:12]=2)[NH:16]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13603778HCID 13603778, compound

Product 1

HCID 13519804HCID 13519804, compound

Conditions

Temperature
50 °C

Procedure

A solution of 2,3-dihydro-2-oxo-1H-indole-7-propandioic acid dimethyl ester (4.6 g, 0.0166 moles) is dissolved in methanol (50 ml) and 1N sodium hydroxide (33.2 ml, 0.0332 mole) is added. The mixture is stirred at 50° C. for 90 minutes then concentrated at reduced pressure. The residue is dissolved in water (75 ml) and methanol (50 ml). The solution is made acidic with excess Dowex 50X-8 acidic ion exchange resin and heated with stirring at 70° C. for 24 hours. The solution is cooled, filtered, and concentrated to dryness to yield 2,3-dihydro-2-oxo-1H-indole-7-propanoic acid. The 2,3-dihydro-2-oxo-1H-indole-7-propanoic acid is purified by flash chromatography on silica (elution with 9:1 dichloromethane:methanol) NMR spectra: ('H-CDCl3) δ 7.30-7.10 (m, 3H), δ 6.50-6.25 (b, 1H) δ 3.80-3.70 (m, 2H), δ 3.70 (5, 2H), δ 3.28-3.22 (m, 2H).

Workup

  1. concentrationthen concentrated at reduced pressure
  2. dissolutionThe residue is dissolved in water (75 ml)
  3. temperatureheated
  4. stirringwith stirring at 70° C. for 24 hours
  5. temperatureThe solution is cooled
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-017b166b1f2e4834a83c705142b92648
Source dataset
uspto-grants-1987_06
Patent number
US04677112

Reaction notes

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