Hydrochloric Acid → HCID 18424235, compound

HRID 863635Notes

Reaction equation

HRID 863635 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]#[N:25].Cl>ClCCCl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:22]2[N:18]([CH3:17])[C:19]([CH2:23][C:24]#[N:25])=[CH:20][CH:21]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424235HCID 18424235, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of 46.4 g. (0.25 mole) of ρ-nitrobenzoyl chloride in 100 ml. 1,2-dichloroethane is added portionwise to a suspension of 32.2 g. (0.25 mole) aluminum chloride in 100 ml. 1,2-dichloroethane. This mixture is added dropwise to a chilled solution of 30.0 g. (0.25 mole) 1-methylpyrrole-2-acetonitrile in 100 ml. 1,2-dichloroethane. After the addition is complete, the mixture is stirred for twenty minutes at room temperature, and then refluxed for four times. It is poured into ice acidified with 3N hydrochloric acid. The organic phase is separated and washed successively with N, N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution. It is then dried over magnesium sulfate and the solvent evaporated in vacuo. The resulting semi-solid residue is triturated with cold methanol from which the product, 5-(ρ-nitrobenzoyl)-1-methylpyrrole-2-acetonitrile, crystallizes. It is removed by filtration and purified by recrystallization from acetone, M.P. 167°-169° C.

Workup

  1. additionThis mixture is added dropwise to a chilled solution of 30.0 g
  2. additionAfter the addition
  3. temperaturerefluxed for four times
  4. additionIt is poured into ice
  5. customThe organic phase is separated
  6. washwashed successively with N, N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution
  7. dry with materialIt is then dried over magnesium sulfate
  8. customthe solvent evaporated in vacuo
  9. customThe resulting semi-solid residue is triturated with cold methanol from which the product, 5-(ρ-nitrobenzoyl)-1-methylpyrrole-2-acetonitrile
  10. customcrystallizes
  11. customIt is removed by filtration
  12. custompurified by recrystallization from acetone, M.P. 167°-169° C.

Sources & evidence

ORD record
ord-a4ab12f6e51741f8bd8e35832d819222
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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