3-Chlorobutanoyl chloride → 1,2,3,4-Tetrahydro-6-nitrobenzofuro[3,2-c]-pyridine

HRID 1274110Notes

Reaction equation

HRID 1274110 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]2[O:8][C:9]3[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]=2[CH2:3]1.ClC(CC(Cl)=O)C>ClCCCl>[N+:15]([C:14]1[C:9]2[O:8][C:5]3[CH2:6][CH2:7][NH:2][CH2:3][C:4]=3[C:10]=2[CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 111710233-Chlorobutanoyl chlorideHCID 221203251,2,3,4-Tetrahydro-2-methyl-6-nitrobenzofuro[3,2-c]pyridine

Product 1

HCID 221203371,2,3,4-Tetrahydro-6-nitrobenzofuro[3,2-c]-pyridineYield 30.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4-tetrahydro-2-methyl-6-nitrobenzofuro[3,2-c]pyridine (0.0224 mol), prepared according to the procedure described in J. Chem. Soc. (C), 1971, p53-60, was dissolved in 1,2-dichloroethane (40 ml), and cooled to 0° C. At this temperature, (1-chloroethyl) acetylchloride (0.0291 mol) was added dropwise. The suspension was stirred and refluxed for 2 hours. 1,2-dichloroethane was evaporated. The mixture was dissolved in methanol, stirred and refluxed for 2 hours, then filtered. Both the filtrate and crystals were treated with 2 N Na2CO3 and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 90/10). The desired fractions were collected and the solvent was evaporated, yielding 1.5 g 1,2,3,4-tetrahydro-6-nitrobenzofuro[3,2-c]-pyridine (intern. 4).

Workup

  1. temperaturerefluxed for 2 hours
  2. custom1,2-dichloroethane was evaporated
  3. dissolutionThe mixture was dissolved in methanol
  4. stirringstirred
  5. temperaturerefluxed for 2 hours
  6. filtrationfiltered
  7. additionBoth the filtrate and crystals were treated with 2 N Na2CO3
  8. extractionthis mixture was extracted with CH2Cl2
  9. customThe separated organic layer was dried
  10. filtrationfiltered
  11. customthe solvent evaporated
  12. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 90/10)
  13. customThe desired fractions were collected
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ce43ec37874b40bab74d2b03aaa4cb57
Source dataset
uspto-grants-2000_12
Patent number
US06156757

Reaction notes

Loading…