4-Nitrobenzoyl chloride → HCID 18424304, compound

HRID 1282335Notes

Reaction equation

HRID 1282335 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=O)=[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]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][C:22]2[N:18]([CH3:17])[C:19]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:21]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424304HCID 18424304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution of 5.5 g. (0.03 mole) of p-nitrobenzoyl chloride in 60 ml. methylene chloride is added to a suspension of 3.9 g. (0.03 mole) aluminum chloride in 20 ml. methylene chloride. The resulting suspension is added dropwise to a chilled (−15° C.) solution of ethyl 1-methylpyrrole-2-acetate in 50 ml. methylene chloride. The solution is stirred for 15 minutes at −10° C. and at room temperature for 15 minutes. The reaction mixture is poured into ice-dilute hydrochloric acid. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and a saturated solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo. A solid, ethyl 5-(p-nitrobenzoyl)-1-methylpyrrole-2-acetate, crystallizes from the remaining oily residue which is isolated by recrystallization from methanol, m.p. 103-106° C.

Workup

  1. additionThe resulting suspension is added dropwise to
  2. additionThe reaction mixture is poured into ice-dilute hydrochloric acid
  3. customThe organic phase is separated
  4. washwashed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid
  5. dry with materiala saturated solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customA solid, ethyl 5-(p-nitrobenzoyl)-1-methylpyrrole-2-acetate, crystallizes from the remaining oily residue which
  8. customis isolated by recrystallization from methanol, m.p. 103-106° C.

Sources & evidence

ORD record
ord-1f16641a1e79435a8179e34aed8fec25
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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