Hydrochloric Acid → 2H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

HRID 372328Notes

Reaction equation

HRID 372328 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].Cl.[CH2:10]([O:12][C:13](=[O:31])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[C:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)[CH3:11].C([BH3-])#N.[Na+]>CO>[ClH:22].[CH2:10]([O:12][C:13]([C:14]1[N:6]([CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:17]2[C:16]=1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18]2)=[O:31])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 60993N,N-DiethylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 54162441o-Benzoyl-p-chloro-phenylglyoxylic acid ethyl ester

Product 1

HCID 30458932H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.5 g. of 2-diethylaminoethylamine in 10 ml. of methanol is treated with 2 ml. of 5-N methanolic hydrochloric acid. Then, there are added successively under argon at 20°-25° C. a solution of 1.6 g. of o-benzoyl-p-chlorophenylglyoxylic acid ethyl ester in 5 ml. of methanol and 0.2 g. of sodium cyanoborohydride and the mixture is stirred for an additional 7 hours at room temperature. While cooling with ice, the mixture is made acidic with concentrated hydrochloric acid, stirred for an additional 0.5 hour at room temperature and evaporated to dryness under reduced pressure. The residue is made alkaline with 1-N sodium hydroxide with addition of ice and extracted with 50 ml. of ether. The ethereal extract is treated with 20 ml. of 0.5-N hydrochloric acid, and the mixture shaken thoroughly. After cooling in an ice-bath, the crystallized hydrochloride is isolated and purified in a manner analogous to that described in Example 1, and there is obtained 5-chloro-2-[2 -(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 248°-250° C. (decomposition).

Workup

  1. additionThen, there are added successively under argon at 20°-25° C. a solution of 1.6 g
  2. temperatureWhile cooling with ice
  3. customevaporated to dryness under reduced pressure
  4. additionwith addition of ice
  5. extractionextracted with 50 ml
  6. extractionThe ethereal extract
  7. additionis treated with 20 ml
  8. stirringof 0.5-N hydrochloric acid, and the mixture shaken thoroughly
  9. temperatureAfter cooling in an ice-bath

Sources & evidence

ORD record
ord-a6c7176ea4f44dce9a479b0119f8b1a3
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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