Toluene → HCID 86746545, compound

HRID 2081687Notes

Reaction equation

HRID 2081687 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=O)[CH2:17][CH2:16]2)(=O)C.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.[C:34]1([CH3:40])C=CC=CC=1>>[C:34]([NH:8][N:7]1[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[C:17]2[CH2:18][C:19]3[C:15]([C:16]1=2)=[CH:14][CH:13]=[CH:21][CH:20]=3)(=[O:30])[CH3:40]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7516PhenylhydrazineHCID 312894N-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 86746545HCID 86746545, compound

Conditions

Temperature
60 °C

Procedure

A solution of phenylhydrazine (4.05 g, 37.5 mM), 5-(N-acetylamino)indan-1-one (Prepared by the method of N. L. Allinger and E. S. Jones (J. Org. Chem., 1962, 27, 70) (5.8 g, 30.7 mM), and 4-toluenesulphonic acid (0.005 g) in toluene (125 cm3) was heated in a Dean Stark apparatus for 2 hours. The reaction mixture was cooled and the product hydrazone filtered off as a pale brown microcrystalline solid (7.3 g, 85%), M.p. 252°-253° C. Finely crushed hydrazone (8.5 g, 30 mM) from the above experiment was added with stirring to a solution of polyphosphoric ester, prepared from phosphorus pentoxide (30 g), chloroform (30 cm3), and diethyl ether (cm3) together for 24 hours. Excess solvents were evaporated off and the residue heated at 60° C. for 45 min. After cooling, the tarry residue was poured into water (150 cm3) and chloroform (40 cm3) and the mixture was agitated vigorously for 10 min. The dark coloured solid which remained was collected and mixed with silica (6 g), and then added to the top of a column of silica (20 g) and the column was eluted with ethyl acetate. A pale yellow solid product was obtained from the eluant. Yield: 2.0 g, 27%. M.p. >240° C. 1H NMR (CDCl3) δ: 2.11 (3H, s), 3.50 (2H, s), 6.95-7.10 (2H, m), 7.33-7.50 (4H, m), 7.67 (1H, br.s).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe product hydrazone filtered off as a pale brown microcrystalline solid (7.3 g, 85%), M.p. 252°-253° C
  3. additionFinely crushed hydrazone (8.5 g, 30 mM) from the above experiment was added
  4. customprepared from phosphorus pentoxide (30 g), chloroform (30 cm3), and diethyl ether (cm3) together for 24 hours
  5. customExcess solvents were evaporated off
  6. temperatureAfter cooling
  7. additionthe tarry residue was poured into water (150 cm3) and chloroform (40 cm3)
  8. stirringthe mixture was agitated vigorously for 10 min
  9. customThe dark coloured solid which remained was collected
  10. additionmixed with silica (6 g)
  11. additionadded to the top of a column of silica (20 g)
  12. washthe column was eluted with ethyl acetate
  13. customA pale yellow solid product was obtained from the eluant

Sources & evidence

ORD record
ord-7520b993d6164e87b219c40039c30754
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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