Pyridine → HCID 11218986, compound

HRID 1633721Notes

Reaction equation

HRID 1633721 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[Cl-].[NH4+]>ClCCl>[CH3:12][C:9]1[C:8]2[C:7](=[O:13])[CH2:6][CH2:5][CH2:4][C:3]=2[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 14024372HCID 14024372, compound

Product 1

HCID 11218986HCID 11218986, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-8-methyltetralone (De, B. Synth. Commun. (1988), 18, 481-486) (0.25 g, 1.4 mmol) in dichloromethane (7 mL) was treated with pyridine (0.35 mL, 4.3 mmol), treated with methanesulfonyl chloride (0.12 mL, 1.5 mmol), stirred at ambient temperature for 1.5 hours, treated with aqueous ammonium chloride solution (20 mL) and extracted with dichloromethane (4×25 mL). The combined dichloromethane extracts were washed with brine, dried (Na2SO4) and concentrated. Purification of the residue on silica gel with ethyl acetate:hexanes 1:1 provided the desired product.

Workup

  1. extractionextracted with dichloromethane (4×25 mL)
  2. washThe combined dichloromethane extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the residue on silica gel with ethyl acetate:hexanes 1:1

Sources & evidence

ORD record
ord-b441a80c278e4e6a9477eb5ff28d4420
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

Loading…