Catechol → HCID 15917387, compound

HRID 1758137Notes

Reaction equation

HRID 1758137 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Cl[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1>C(Cl)Cl>[C:3]1([O:4][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=1[O:2][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 289CatecholHCID 276852,5-Dichloropyridine

Product 1

HCID 15917387HCID 15917387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.0 grams (0.027 mole) catechol and 9.0 grams (0.06 mole) 2,5-dichloropyridine was heated as a melt under nitrogen for 7 hours at 175° followed by heating at 200° for 5 hours. The black residue was dissolved in a minimum amount of methylene chloride and chromatographed through a silica gel column using methylene chloride as the eluent. From the initial fractions, the desired product was isolated. Yield 1.5 g, m.p. 82°-84°; NMR (CDCl3): δ6.70 (d, 2H, ArH), 7.30 (s, 4H, ArH), 7.60 (AB quartet, 2H, ArH), 8.05 (d, 2H, ArH); ir (Nujol): 6.30 (C=N), 9.90, 11.95, 13.10 microns.

Workup

  1. temperaturewas heated as a melt under nitrogen for 7 hours at 175°
  2. temperatureby heating at 200° for 5 hours
  3. customchromatographed through a silica gel column

Sources & evidence

ORD record
ord-4b79354dce7441f08d4b14e0ffa5c780
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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