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

HRID 551781Notes

Reaction equation

HRID 551781 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]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]>O1CCCC1>[N:1]1([C:19]([O:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 178488194-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g of 1,2,3,4-tetrahydroquinoline, 10.46 ml of triethylamine, 270 ml of tetrahydrofuran and then 15.13 g of para-nitrophenyl chloroformate are introduced into a 1 l round-bottomed flask. The reaction medium is stirred at ambient temperature for two hours and then filtered. The solvent is evaporated under reduced pressure and the residue is taken up in dichloromethane and washed with a 2N aqueous hydrochloric acid solution and then twice with water. The organic phase is dried over magnesium sulfate and the solvent is evaporated under reduced pressure to result in 21.5 g of 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate.

Workup

  1. filtrationfiltered
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with a 2N aqueous hydrochloric acid solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customto result in 21.5 g of 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate

Sources & evidence

ORD record
ord-916d9988016143618961d3606d0d61f0
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

Loading…