Pyridine → 3-(3-Chloro-4-methoxyphenyl)propan-1-amine

HRID 431781Notes

Reaction equation

HRID 431781 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.S(Cl)([Cl:14])(=O)=O.[N:16]1C=CC=[CH:18][CH:17]=1>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][CH2:18][CH2:17][NH2:16])=[CH:5][C:4]=1[Cl:14]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 122776873-(3-Chloro-4-methoxyphenyl)propan-1-amineYield 77%

Procedure

4-Methoxy-benzaldehyde (Aldrich) (42 g, 0.31 mole) and pyridine (0.6 ml, catalytic) were stirred together under nitrogen and sulfuryl chloride (51 g, 0.37 mole) added over 30 min, maintaining the internal temperature of the reaction at between 25 and 30° C. There was a vigorous evolution of gas. The mixture was stirred at room temperature for a further 30 min, and then warmed to 70° C. for 4 h. Excess reagents were removed by evaporation in vacuo and the residue taken up in 50 ml diisopropyl ether and poured onto 500 ml hexane with vigorous stirring, from which the product precipitates. The solid was filtered off and washed with hexane and then dried in vacuo to give the title product (40.3 g, 77%), m.p. 55-56° C.; 1HNMR (400 MHz, CDCl3) δ: 3.99 (s, 3H), 7.05 (dd, 1H), 7.91 (d, 1H), 9.86 (s, 1H); Anal. Found: C, 56.13; H, 4.14%. C8H7CIO2 requires C, 56.33; H, 4.14%.

Workup

  1. temperaturemaintaining
  2. customthe internal temperature of the reaction at between 25 and 30° C
  3. temperaturewarmed to 70° C. for 4 h
  4. customExcess reagents were removed by evaporation in vacuo
  5. additionpoured onto 500 ml hexane with vigorous stirring, from which the product
  6. customprecipitates
  7. filtrationThe solid was filtered off
  8. washwashed with hexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5833138e8cfd4ffe909c6db709d331c9
Source dataset
uspto-grants-2003_12
Patent number
US06660756B2

Reaction notes

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