Pyridinium chloride → HCID 59770021, compound

HRID 2218634Notes

Reaction equation

HRID 2218634 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.Cl.N1C=CC=CC=1>Cl>[CH:18]1[C:9]2[CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:7](=[CH:6][C:5]3[CH:4]=[C:3]([OH:2])[CH:24]=[CH:23][CH:22]=3)[C:8]=2[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 59770540HCID 59770540, compound

Product 1

HCID 59770021HCID 59770021, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Stir a molten mixture of 5-(3-methoxy-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (1.11 g, 3.55 mmol) and pyridine hydrochloride (10 g, 87 mmol) at 215° C. for 40 min. Cool the reaction mixture to 100° C., dilute with 1N HCl, and extract with ethyl acetate. Dry organics (MgSO4), filter, and concentrate to a brown oil containing the title compound. Purification via silica gel chromatography (1:6 ethyl acetate:hexanes) affords 940 mg (89%) of a tan oil. 1H NMR (CDCl3) δ 2.76-3.63 (br m, 4H), 4.59 (s, 1H), 6.45 (s, 1H), 6.64 (m, 2H), 6.75 (s, 1H), 6.99-7.52 (m, 9H); MS (ES) 299 (M+H), 297 (M−H). HPLC shows 97% purity.

Workup

  1. extractionextract with ethyl acetate
  2. filtrationDry organics (MgSO4), filter
  3. concentrationconcentrate to a brown oil
  4. additioncontaining the title compound
  5. customPurification via silica gel chromatography (1:6 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fbc62f3b1cad41c59e877a3e28cfd274
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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