1,2,3,4-Tetrahydroisoquinoline → 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1936602Notes

Reaction equation

HRID 1936602 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20]>ClCCl>[N+:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19]([N:2]2[C:1]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:5][CH2:4][CH2:3]2)=[O:20])=[CH:27][CH:26]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 178488194-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylateYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetrahydroisoquinoline (3.99 g, 30 mmol) in triethyl amine(6 g, 60 mmol) and dichloromethane(150 mL) cooled in ice bath was added p-nitrophenyl chloroformate (6.06 g, 30 mmol) drop wise over a period of 1 h. The reaction mixture was stirred at room temperature for 3 h and then washed with water (3×100 mL), dried over sodium sulfate and concentrated to afford an oil which was triturated with ether:hexane to afford the titled compound as yellow solid (5.9 g, 65%).

Workup

  1. washwashed with water (3×100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford an oil which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-2ae9f184fe9a474a8dd86cc8194956ce
Source dataset
uspto-grants-2002_05
Patent number
US06391877B1

Reaction notes

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