Methylamine → Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 1282355Notes

Reaction equation

HRID 1282355 reaction equation
[CH3:1][NH2:2].[CH3:3][CH2:4][O:5][C:6]([CH2:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)=[O:7].Cl[CH2:18][C:19](=O)[CH3:20]>>[CH3:1][N:2]1[CH:18]=[C:19]([CH3:20])[C:8]([C:6]([O:5][CH2:4][CH3:3])=[O:7])=[C:9]1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 6571ChloroacetoneHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 118460Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Procedure

To a solution of 500 ml. of 25% aqueous methylamine is added 93 g. (0.46 mole) of diethyl acetone-dicarboxylate. To the mixture is added 72 g. (0.782 mole) of chloroacetone over a 10-minute period. The temperature is kept below 60° C. by external cooling. After 2 hours, the mixture is poured into ice-hydrochloric acid. The solid is collected by filtration, washed with water and air dried. It is recrystallized from hexane to give ethyl 1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate as a white solid, m.p. 71-72° C. Anal. Calcd. for C13H19NO4: C, 61.64; H, 7.56; N, 5.53%. Found: C, 61.64; H, 7.64; N, 5.71%.

Workup

  1. additionTo the mixture is added 72 g
  2. customis kept below 60° C. by external cooling
  3. filtrationThe solid is collected by filtration
  4. washwashed with water and air
  5. customdried
  6. customIt is recrystallized from hexane

Sources & evidence

ORD record
ord-0ed762b444f74ac7862b6958664a7018
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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