1,2,3,4-Tetrahydroisoquinoline → HCID 23434368, compound

HRID 2121839Notes

Reaction equation

HRID 2121839 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1>CN1CCCC1>[CH3:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([CH3:8])=[CH:7][C:2]=1[N:14]1[CH2:15][CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 23434368HCID 23434368, compound

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-chloro-2,5-dimethyl-4-nitrobenzene (1.65 g) and 1,2,3,4-tetrahydroisoquinoline (5 ml) in N-methylpyrrolidine (5 ml) is stirred at 140° C. for 15 h. Dilution in water followed by extraction with diethyl ether and chromatography on silica (eluent: 1/1 petroleum ether/diethyl ether) of the dried and evaporated organic phase gives 2-(2,5-dimethyl-4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. extractionDilution in water followed by extraction with diethyl ether and chromatography on silica (eluent: 1/1 petroleum ether/diethyl ether) of the
  2. customdried
  3. customevaporated organic phase

Sources & evidence

ORD record
ord-394fcbfa9d8a434cb453da1de8272c40
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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