Pyridine → HCID 68426884, compound

HRID 1927530Notes

Reaction equation

HRID 1927530 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][C:11](=[O:24])[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([Br:19])=[C:14]([S:20](Cl)(=[O:22])=[O:21])[CH:13]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:24])[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([Br:19])=[C:14]([S:20](=[O:21])(=[O:22])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 58012-AminophenolHCID 86617089HCID 86617089, compound

Product 1

HCID 68426884HCID 68426884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 2-aminophenol (2.5 g, 22.9 mmol) in dry methylene chloride (10 mL) was added to a mixture of 4-bromo-3-chlorosulfonyl-5-methyl-benzoic acid methyl ester (7.18 g, 22.9 mmol) and dry pyridine (10 mL, 124.7 mmol) in methylene chloride (40 mL). The reaction mixture was stirred for 1 h at 10° C. and at room temperature overnight. It was concentrated, treated with 10% HCl (100 mL) and extracted with 1-butanol. The organic layer was washed with water, brine, dried, concentrated, treated with methanolic HCl (60 ml) and refluxed for 3 h. The reaction mixture was concentrated, treated with 10% aqueous sodium bicarbonate solution to alkaline pH and extracted using ethyl acetate. The organic layer was washed with water, brine, dried and purified, using flash chromatography (silica gel, 10% ethyl acetate/pet ether) to obtain the title compound. Yield: 2.2 g, (24%); 1H NMR (CDCl3): δ 2.4 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 6.6 (t, 1H, Ar), 6.72 (t, 1H, Ar), 6.74 (d, 1H, Ar), 7.2 (d, 1H, Ar), 7.94 (s, 1H, OH), 7.96 (s, 1H, Ar), 8.5 (s, 1H, Ar); MS: m/e (EI+) 400 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with 10% HCl (100 mL)
  3. extractionextracted with 1-butanol
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. additiontreated with methanolic HCl (60 ml)
  8. temperaturerefluxed for 3 h
  9. concentrationThe reaction mixture was concentrated
  10. additiontreated with 10% aqueous sodium bicarbonate solution
  11. extractionextracted
  12. washThe organic layer was washed with water, brine
  13. customdried
  14. custompurified

Sources & evidence

ORD record
ord-a3c3f7e17cd84b81a84b5d83dfacd6e8
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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