Hydrochloric Acid → HCID 67222804, compound

HRID 2088734Notes

Reaction equation

HRID 2088734 reaction equation
[CH2:1]([NH2:3])[CH3:2].CS(O[CH2:9][CH2:10][C:11]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:12]=1[CH2:13]CS([O-])(=O)=O)(=O)=O.Cl>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[CH2:9][CH2:10][C:11]2[C:12](=[CH:19][CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=2)[CH2:13]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 71650875HCID 71650875, compound

Product 1

HCID 67222804HCID 67222804, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7.65 mL of ethylamine was dropwise added to a chloroform (15 mL) solution of 1.08 g of 2-{2-[(methylsulfonyl)oxyethyl}-4-nitrobenzylmethanesulfonate, which had been produced according to the method described in Journal of Organic Chemistry, Vol. 63, pp. 4116-4119, and stirred for 12 hours. 1 N hydrochloric acid was added to the reaction solution, and stirred, and then the aqueous layer was separated. Aqueous 5 N sodium hydroxide solution was added to the resulting aqueous layer, extracted with chloroform, and the organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated away. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 210 mg of 2-ethyl-6-nitro-1,2,3,4-tetrahydroisoquinoline as a yellow solid.

Workup

  1. customhad been produced
  2. stirringstirred
  3. customthe aqueous layer was separated
  4. additionAqueous 5 N sodium hydroxide solution was added to the resulting aqueous layer
  5. extractionextracted with chloroform
  6. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  7. customthe solvent was evaporated away
  8. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b25c7d43562a4a5496c2d13216ff3a7c
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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