Hydrochloric Acid → Methyl [5-(4-methoxybenzoyl)-1-methyl-1H-pyrrol-2-yl]acetate

HRID 1606140Notes

Reaction equation

HRID 1606140 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl>C(Cl)Cl>[C:1]([C:21]1[N:17]([CH3:16])[C:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:20]=1)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 103992Methyl 1-methylpyrrol-2-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424261Methyl [5-(4-methoxybenzoyl)-1-methyl-1H-pyrrol-2-yl]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 17.0 g. (0.1 mole) of p-anisoyl chloride and 13.3 g. (0.1 mole) of aluminum chloride in 200 ml. of methylene chloride is added over 5 minutes to a solution of methyl 1-methylpyrrole-2-acetate in 100 ml. of methylene chloride at ice bath temperature. The mixture is stirred for 25 minutes and poured into ice acidified with dilute hydrochloric acid. The organic layer is separated and the aqueous layer is washed with methylene chloride. The combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine and then dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo to give a dark oily residue which is crystallized from 40 ml. of cold methanol. The solid is collected by filtration, washed with cold methanol and recrystallized from methanol to give white crystalline methyl 5-(p-anisoyl)-1-methylpyrrole-2-acetate, m.p. 104°-105°C.

Workup

  1. additionpoured into ice
  2. customThe organic layer is separated
  3. washthe aqueous layer is washed with methylene chloride
  4. washThe combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated in vacuo
  7. customto give a dark oily residue which
  8. customis crystallized from 40 ml
  9. filtrationThe solid is collected by filtration
  10. washwashed with cold methanol
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4d9f702c787b4d81896c6f6ff7884b92
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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