Sodium Carbonate → 2-(2-Aminoethyl)-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester

HRID 372321Notes

Reaction equation

HRID 372321 reaction equation
Br.[CH2:2]([O:4][C:5]([C:7]1[N:8]([CH2:23][CH2:24][NH2:25])[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]2[C:15]=1[CH:14]=[CH:13][C:12]([Cl:16])=[CH:11]2)=[O:6])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+]>CCOCC>[CH2:2]([O:4][C:5]([C:7]1[N:8]([CH2:23][CH2:24][NH2:25])[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]2[C:15]=1[CH:14]=[CH:13][C:12]([Cl:16])=[CH:11]2)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 70621110HCID 70621110, compound

Product 1

HCID 541877222-(2-Aminoethyl)-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In order to obtain the free base, the hydrobromide obtained according to the previous paragraph is treated with 2-N sodium carbonate in the presence of ether. The ethereal extract, shielded from light, is washed with water, dried over sodium sulfate and evaporated. The residue crystallizes on trituration with ether. Recrystallization from ether/hexane yields almost colorless crystals of 2-(2-aminoethyl)-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester; melting point 84°-86° C.

Workup

  1. customIn order to obtain the free base
  2. extractionThe ethereal extract
  3. washis washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue crystallizes on trituration with ether
  7. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-91e067966ebc41939233ae7bbeff69d6
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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