Hydrochloric Acid → 1-[2-(p-Carboxyphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

HRID 1719381Notes

Reaction equation

HRID 1719381 reaction equation
C([O:3][C:4]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:28][CH:29]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 202681801-[2-(p-Ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

Product 1

HCID 202681781-[2-(p-Carboxyphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[2-(p-ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole (1.66 g) and 3N sodium hydroxide (20 ml) in absolute ethanol (20 ml) is stirred and refluxed for 2 hours. The solution is cooled and acidified to pH 3 with 3N hydrochlorid acid. The precipitate which forms (m.p.>300°) is collected. This solid is dissolved in a saturated sodium bicarbonate solution and the carboxylic acid is reprecipitated by acidifying the solution to pH 5 with 3N hydrochloric acid. The white solid is collected to give 1-[2-(p-carboxyphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole; NMR (DMSO): δ2.17 (s, 3H), 4.30 (m, 4H).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe solution is cooled
  3. customis collected
  4. dissolutionThis solid is dissolved in a saturated sodium bicarbonate solution
  5. customthe carboxylic acid is reprecipitated
  6. customThe white solid is collected

Sources & evidence

ORD record
ord-a633b87f7a7943218837974629b9df7d
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

Loading…