Potassium Hydroxide → 3-(5-cyano-1H-indol-3-yl)propanoic Acid

HRID 1419612Notes

Reaction equation

HRID 1419612 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[NH:8][CH:7]=1.[OH-].[K+]>CO>[C:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][C:3]([OH:17])=[O:2])#[N:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19921624methyl 3-(5-cyano-1H-indol-3-yl)propanoate

Product 1

HCID 104432213-(5-cyano-1H-indol-3-yl)propanoic AcidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methy-5-cyanoindole-3-propionate (200 mg) was saponified in MeOH (10 mL)/KOH (150 mg, 0.88 mmol) at rt for 18 h. The solution was concentrated in vacuo, dissolved in water and washed with chloroform. The acidic layer was acidified and extracted with ethyl acetate, dried with Na2SO4, filtered and concentrated in vacuo to afford 188 mg of product. 1H NMR (CD3OD) δ ppm 2.83 (t, 2H, J=6.6 Hz), 4.43 (t, 2H, J=6.6 Hz), 6.6 (nd,1H, J3.2 Hz), 7.42 (d, 2H, J=7.3 Hz), 7.43 (s, 1H), 7.61 (d, 1H, J=7.3 Hz), 7.99 (s, 1H); LRMS ESI (M+H)+ 215.

Workup

  1. customat rt
  2. customfor 18 h
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutiondissolved in water
  5. washwashed with chloroform
  6. extractionextracted with ethyl acetate
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47c5ec1310f14dc8acc53322f1241a63
Source dataset
uspto-grants-1999_03
Patent number
US05886191

Reaction notes

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