Ammonium Hydroxide → 3-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 1973310Notes

Reaction equation

HRID 1973310 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH2:9]([O:11][C:12](=[O:30])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=O)[CH3:10].[OH-].[NH4+]>C(O)=O>[ClH:28].[CH2:9]([O:11][C:12]([C:13]1[N:6]([CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:16]2[C:15]=1[CH:20]=[CH:19][CH:18]=[CH:17]2)=[O:30])[CH3:10]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 60993N,N-DiethylethylenediamineHCID 53699063HCID 53699063, compound

Product 1

HCID 706202883-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 0.83 g. of formic acid and 1.05 g. of 2-diethylaminoethylamine is treated at room temperature with 0.95 g. of [o-(p-chlorobenzoyl)phenyl]glyoxylic acid ethyl ester and subsequently stirred at 140° C. for 2 hours. After cooling, the obtained solution is made alkaline with 2-N ammonium hydroxide with addition of ice and extracted with ether. The extract, shielded from daylight, is washed with water, dried over sodium sulfate, concentrated and chromatographed on 70 g. of silica gel with ether as the eluant. The homogeneous fractions are combined, concentrated to a volume of 15-20 ml. and treated with ethereal hydrochloric acid. The crystallized hydrochloride is removed by filtration and washed with ether, and there is obtained 3-(p-chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 202°-204° C. (decomposition). Recrystallization from methylene chloride/ether does not increase the melting point.

Workup

  1. additionA mixture of 0.83 g
  2. temperatureAfter cooling
  3. additionwith addition of ice
  4. extractionextracted with ether
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on 70 g
  9. concentrationconcentrated to a volume of 15-20 ml
  10. additionand treated with ethereal hydrochloric acid
  11. customThe crystallized hydrochloride is removed by filtration
  12. washwashed with ether

Sources & evidence

ORD record
ord-d479646bdab447c1bd60acae5e438cff
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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