Hydrochloric Acid → HCID 18424171, compound

HRID 1282337Notes

Reaction equation

HRID 1282337 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[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][CH2:26][CH3:27])=[O:24].Cl>C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([C:21]2[N:17]([CH3:16])[C:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:20]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 801724-Cyanobenzoyl chlorideHCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424171HCID 18424171, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 5.0 g. (0.03 mole) of p-cyanobenzoyl chloride in 60 ml. of methylene chloride is added to a suspension of 40 g. of aluminum chloride in 30 ml. methylene chloride. The resulting mixture is added dropwise to a chilled solution of 5.0 g. (0.03 mole) of ethyl 1-methylpyrrole-2-acetate in 15 ml. of methylene chloride. The resulting mixture is stirred at room temperature for 20 minutes, and then poured into ice acidified with dilute hydrochloric acid. The organic phase is separated, washed successively with N,N-dimethylaminopropylamine, 3N hydrochloric acid and brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo. The resulting solid, which separates from the oily residue on standing, is recrystallized from methanol to give pure ethyl 5-(p-cyanobenzoyl)-1-methylpyrrole-2-acetate, m.p. 117-120° C.

Workup

  1. additionThe resulting mixture is added dropwise to a chilled solution of 5.0 g
  2. additionpoured into ice
  3. customThe organic phase is separated
  4. washwashed successively with N,N-dimethylaminopropylamine, 3N hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated in vacuo
  7. customis recrystallized from methanol

Sources & evidence

ORD record
ord-b1ab4576ddec4a7daffabd0d26fe8dcc
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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