Hydrochloric Acid → 3-(1-Methyl-2-pyrrolylcarbonyl)propionic acid

HRID 66512

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[O:8].CN1C=CC=C1C(N1CCOCC1)C#N.[C:24]([O:28]CC)(=[O:27])[CH:25]=[CH2:26].Cl>>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([CH2:26][CH2:25][C:24]([OH:28])=[O:27])=[O:8]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 8821Ethyl Acrylate

HCID 145041-Methyl-1H-pyrrole-2-carbaldehyde

HCID 20529962(1-methyl-1H-pyrrol-2-yl)(morpholin-4-yl)acetonitrile

Product 1

HCID 125040543-(1-Methyl-2-pyrrolylcarbonyl)propionic acid

Procedure

As for Example 6, 1-methyl-2-pyrrolecarboxaldehyde is converted to α-(1-methyl-2-pyrrolyl)-4-morpholineacetonitrile. The preceding compound is reacted with ethyl acrylate and the resulting 1,4-addition product is heated at 100° C. with 6 N hydrochloric acid to give 3-(1-methyl-2-pyrrolylcarbonyl)propionic acid.

Sources & evidence

ORD record: ord-83427d926c2b4611b3276d880cadd921
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04342690

Linked notes

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