Ammonia → 2-(5-Ethyl-2-pyrrolyl)glycine

HRID 1389128Notes

Reaction equation

HRID 1389128 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1)[CH3:2].O.[C:9]([OH:13])(=[O:12])[CH:10]=O.[NH3:14].Cl>>[CH2:1]([C:3]1[NH:4][C:5]([CH:10]([C:9]([OH:13])=[O:12])[NH2:14])=[CH:6][CH:7]=1)[CH3:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1370752-EthylpyrroleHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 202982512-(5-Ethyl-2-pyrrolyl)glycineYield 43%

Procedure

2-Ethylpyrrole (4.75 g., 0.05 mole) was added dropwise to a stirred solution of glyoxylic acid hydrate (2.3 g., 0.025 mole) in 0.880 sp. gr. ammonia solution (25 ml.) at 50°. The mixture was stirred at 50° for 4 hours, then cooled, acidified to pH 5.5 with concentrated hydrochloric acid and filtered. The resulting solid was washed with water, triturated with cold, then hot; methanol and dried in vacuo to afford DL-2-(5-ethyl-2-pyrrolyl)glycine (1.8 g., 43%), M.P. 188° (decomp.).

Workup

  1. customat 50°
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe resulting solid was washed with water
  5. customtriturated with cold, then hot
  6. dry with materialmethanol and dried in vacuo

Sources & evidence

ORD record
ord-c8a99488294a416cb1bf19e523e07861
Source dataset
uspto-grants-1981_01
Patent number
US04243672

Reaction notes

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