Ethylene Glycol → HCID 12595983, compound

HRID 1701281Notes

Reaction equation

HRID 1701281 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[CH2:4][N:5]1C=[CH:8][CH:7]=[C:6]1C#N.[OH-:17].[K+].[CH2:19]([OH:22])[CH2:20]O>O>[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[CH2:4][N:5]1[CH:6]=[CH:7][CH:8]=[C:20]1[C:19]([OH:22])=[O:17]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 12595980HCID 12595980, compound

Product 1

HCID 12595983HCID 12595983, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 g. of 1-(2-amino-5-chlorobenzyl)-2-pyrrolecarbonitrile, 8 g. of 86% potassium hydroxide and 50 ml. of ethyleneglycol is heated in an oil bath at 170° C. for 2 hours. The mixture is partly cooled and diluted with 80 ml. of water. The mixture is cooled for about 3 hours and then filtered. The filtrate is treated with acetic acid to pH 4-5 giving a precipitate which is collected and washed with water. This solid is further purified by dissolving in dilute alkali and reprecipitating with acetic acid, giving 1-(2-amino-5-chlorobenzyl)-2-pyrrolecarboxylic acid.

Workup

  1. additionA mixture of 8 g
  2. temperatureThe mixture is partly cooled
  3. additiondiluted with 80 ml
  4. temperatureThe mixture is cooled for about 3 hours
  5. filtrationfiltered
  6. additionThe filtrate is treated with acetic acid to pH 4-5
  7. customgiving a precipitate which
  8. customis collected
  9. washwashed with water
  10. customThis solid is further purified
  11. dissolutionby dissolving in dilute alkali
  12. customreprecipitating with acetic acid

Sources & evidence

ORD record
ord-b2407d5f9b894a22a61ee45b8112fa47
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

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