Methylamine → Methyl 3-(3-cyano-1,5-dimethylpyrrol-2-yl)benzoate

HRID 399847Notes

Reaction equation

HRID 399847 reaction equation
[C:1]([CH2:3][C:4]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=O)#[N:2].Cl.C([N:19]([CH2:22][CH3:23])[CH2:20]C)C.CN.Cl[CH2:27]C(=O)C>C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([C:3]1[CH:27]=[C:22]([CH3:23])[N:19]([CH3:20])[C:4]=1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])#[N:2]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 6571ChloroacetoneHCID 11130Triethylamine hydrochlorideHCID 18945177Methyl 3-(cyanoacetyl)benzoate

Product 1

HCID 18945303Methyl 3-(3-cyano-1,5-dimethylpyrrol-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the stirring mixture of methyl 3-(cyanoacetyl)benzoate (2.0 g), triethylamine (1.4 ml), triethylamine hydrochloride (1.4 g) and 40% aqueous methylamine (0.93 ml) was added chloroacetone (0.86 ml) at ambient temperature and the mixture was stirred for 2 hours at the same temperature. To the reaction mixture was added ethyl acetate and the mixture was washed with water. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give methyl 3-(3-cyano-1,5-dimethylpyrrol-2-yl)benzoate (1.6 g).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8d0b878e85e94169b8bdd4cea3bbf8fc
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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