Dichloromethane → 3(R,S)Ethoxycarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 863304Notes

Reaction equation

HRID 863304 reaction equation
[OH-].[Na+].Cl[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH2:11]1.C(Cl)Cl>C1(C)C=CC=CC=1>[CH2:7]([O:6][C:4]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH2:11]1)=[O:5])[CH3:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 40551181,2,3,4-Tetrahydroquinolin-3-amine

Product 1

HCID 196978033(R,S)Ethoxycarbonylamino-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 ml of a 10% sodium hydroxide solution and 0.34 ml of ethyl chloroformate are added in succession to a solution of 0.5 g of 3(R,S)-amino-1,2,3,4-tetrahydroquinoline in 6 ml of toluene, while stirring vigorously, and when the addition has ended, the mixture is stirred for a further 5 min. Customary working up and chromatography of the crude product over 25 g of silica gel with methylene chloride as the mobile phase gives the title compound: Rf (P)=0.78; MS: M+ =220.

Workup

  1. additionwhen the addition
  2. stirringthe mixture is stirred for a further 5 min

Sources & evidence

ORD record
ord-96b2a6f443f945e5a379238ff4162046
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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