Acetic Acid → HCID 12399293, compound

HRID 1284101Notes

Reaction equation

HRID 1284101 reaction equation
[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17](N)=[O:18])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl.C(O)(=[O:23])C>>[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:18])=[O:23])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12399254HCID 12399254, compound

Product 1

HCID 12399293HCID 12399293, compound

Procedure

A mixture of 1 g of 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetamide, 5 ml of glacial acetic acid and 5 ml of concentrated hydrochloric acid is heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, and water is added to the residue. The mixture is alkalified with 10% sodium hydroxide, and then filtered. The filtrate is adjusted to pH 6 by addition of 10% hydrochloric acid. The crystalline precipitate is filtered off and washed with water to give 0.8 g of 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetic acid as colorless crystals melting at 220°-222°C with decomposition.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. distillationThe solvent is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. filtrationfiltered
  6. additionThe filtrate is adjusted to pH 6 by addition of 10% hydrochloric acid
  7. filtrationThe crystalline precipitate is filtered off
  8. washwashed with water

Sources & evidence

ORD record
ord-e4607730dd63463481241f193249cd50
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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