Chloroform → HCID 15082722, compound

HRID 2081679Notes

Reaction equation

HRID 2081679 reaction equation
C1(=O)C2C(=CC=CC=2)CC1.CO[C:13]1[CH:21]=[CH:20][C:19]2[NH:18][C:17]3[C:22]4[C:27]([CH2:28][C:16]=3[C:15]=2[CH:14]=1)=[CH:26][CH:25]=[CH:24][CH:23]=4.C(Cl)(Cl)[Cl:30]>>[Cl:30][C:20]1[C:19]2[NH:18][C:17]3[C:22]4[C:27]([CH2:28][C:16]=3[C:15]=2[CH:14]=[CH:13][CH:21]=1)=[CH:26][CH:25]=[CH:24][CH:23]=4

Participants

4

Reactant 3

HCID 6212ChloroformHCID 67351-IndanoneHCID 15082721HCID 15082721, compound

Product 1

HCID 15082722HCID 15082722, compound

Procedure

The o-chlorophenylhydrazone of 1-indanone (650 mg, 2.5 mmol) was boiled in a chloroform solution of polyphosphonate ester (see the preparation of 5,10-dihydro-8-methoxyindeno[1,2-b]indole) for 30 minutes. The solvent was removed, and the residue stirred in water (75 cm3) for 1 hour. Extraction into diethylether gave a green solution which was washed with water, dried (MgSO4), and evaporated. Purification by column chromatography (Rf [5% EtOAc/petrol (60°-80° C.)]0.5), gave the title compound as a colourless solid. Yield 500 mg, (82%). M.p. 139° C. 1H NMR (CDCl3) δ: 3.72 (2H,s,), 7.0-7.6 (7H, m,), 8.5 (1H, br,).

Workup

  1. customThe solvent was removed
  2. extractionExtraction into diethylether
  3. customgave a green solution which
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification by column chromatography (Rf [5% EtOAc/petrol (60°-80° C.)]0.5),

Sources & evidence

ORD record
ord-305a36181280489099c53f4675068e55
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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