Hydrochloric Acid → 1-methyl-1H-pyrrole-3-carboxylic acid

HRID 2292843Notes

Reaction equation

HRID 2292843 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([O:9]CC)=[O:8])=[CH:3]1.[OH-].[Na+].Cl.[Cl-].[Na+]>>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3]1

Participants

5

Conditions

Temperature
0 °C

Procedure

7.66 g (50 mmole) of ethyl 1-methyl-3-pyrrolecarboxylate prepared in Example 1 and 37.5 ml (75 mmole) of 2N sodium hydroxide aqueous solution were charged into a reaction vessel and refluxed for two hours. The reaction mixture was cooled to 0° C. and about 7 ml of 6N hydrochloric acid solution was added while stirring. After the addition of 15 g of sodium chloride, the mixture was stirred for one hour over an ice-acetone bath to collect precipitated crystals. The crystals were washed with cold water and dried under reduced pressure to obtain 5.77 g (yield 92.2%) of colorless or light-yellow powdery crystals of 1-methyl-3-pyrrolecarboxylic acid.

Workup

  1. temperaturerefluxed for two hours
  2. stirringthe mixture was stirred for one hour over an ice-acetone bath
  3. customto collect
  4. customprecipitated crystals
  5. washThe crystals were washed with cold water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-747b45be66664507851ea84f0a5ecd59
Source dataset
uspto-grants-1997_11
Patent number
US05684161

Reaction notes

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