Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 5-Acetamino-2-indoleacrylic acid

HRID 1455893Notes

Reaction equation

HRID 1455893 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:14]=O)=[CH:8]2)[C:2]([CH3:4])=[O:3].C[O:17][C:18](=[O:39])[CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:14]=[CH:19][C:18]([OH:39])=[O:17])=[CH:8]2)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 107981515-Acetamino-2-indolecarboxaldehyde

Product 1

HCID 543289055-Acetamino-2-indoleacrylic acidYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16 (340 mg, 0.7 mmol) was added to a solution of methyl(triphenylphosphoranylidene)acetate (2|57 mg, 0.77 mmol) in toluene (30 mL) and the reaction mixture was heated to reflux for 3 days. The solvent was removed after cooled to room temperature. Ethyl acetate (10 mL) was added to the residue and the resulted precipitate 17 was filtered. MS (ion spray) (M+H) 259. Without further purification 17 was dissolved in DMF (3 mL) and methanol (5 mL) was added. 3N NaOH solution (2 mL) was added and the reaction mixture was stirred overnight. The solvent was removed and water (10 mL) was added. The solution was neutralized using 20% HCl. The resulting precipitate was filtered and washed with water. 44 mg (26% yield) of yellow solid 18 was obtained. mp: 238°-239° C. 1H NMR (DMSO-d6, ppm): 12.25 (brs, 1 H, COOH), 11.42 (s, 1 H, NH), 9.74 (s, 1 H, NH), 7.88 (s, 1 H, Ar--H), 7.55-7.50 (d, 1 H, J=16.0 Hz, CH=CH), 7.28 (s, 2 H, Ar--H) 6.80 (d, 1 H, J=2.0 Hz, Ar--H), 6.44-6.40 (d, 1 H, J=15.8 Hz, CH=CH), 2.03 (s, 3 H, CH3), Anal. (C13H12N2O3 0.3H2O), C, H, N.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 days
  3. customThe solvent was removed
  4. additionEthyl acetate (10 mL) was added to the residue
  5. filtrationthe resulted precipitate 17 was filtered
  6. customWithout further purification 17
  7. dissolutionwas dissolved in DMF (3 mL)
  8. additionmethanol (5 mL) was added
  9. addition3N NaOH solution (2 mL) was added
  10. customThe solvent was removed
  11. additionwater (10 mL) was added
  12. filtrationThe resulting precipitate was filtered
  13. washwashed with water

Sources & evidence

ORD record
ord-e64d01e3359e4634a6cdec5a7630af72
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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