Einecs 211-027-4 → HCID 14032095, compound

HRID 2081682Notes

Reaction equation

HRID 2081682 reaction equation
C[O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:7]=1[CH2:6]2.[Cl-].[NH+]1C=CC=CC=1>>[OH:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:7]=1[CH2:6]2

Participants

3

Reactant 2

HCID 69401Einecs 211-027-4HCID 14032101HCID 14032101, compound

Product 1

HCID 14032095HCID 14032095, compound

Conditions

Temperature
200 °C

Procedure

5,10-Dihydro-2-methoxy-1,3-dimethylindeno[1,2-b]indole (2.4 g, 9.1 mmol) and pyridinium chloride (5.8 g) were mixed and heated to 200° C. for 30 minutes. The reaction mixture was cooled, and partitioned between ethyl acetate and water. The organic phase was washed three times with 2 M hydrochloric acid, and then three times with water, and then dried (MgSO4). The solvent was removed in vacuo, and the residue purified by column chromatography to give the title compound as colourless prisms. Yield: 1.5 g (66%). M.p. 190° C. (from dichloromethane). 1H NMR (DMSO-d6) δ: 2.25 (3H,s,), 2.26 (3H,s,), 3,50 (2H, s,), 6.9-7.5 (5H, m,), 8.16 (1H, br,), 11.33 (1H, br,).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed three times with 2 M hydrochloric acid
  4. dry with materialthree times with water, and then dried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-e16ded51050449939056b7fabea17944
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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