Triethylamine → HCID 87302908, compound

HRID 551783Notes

Reaction equation

HRID 551783 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.C([N:25](CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.O>[N:13]1([NH:25][C:2]([Cl:1])=[O:4])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 94429TriphosgeneHCID 516892Sodium Bicarbonate

Product 1

HCID 87302908HCID 87302908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4.9 g of triphosgene are added to a solution of 5.5 g of 1,2,3,4-tetrahydroquinoline and 6.4 ml of triethylamine in 213 ml of dichloromethane at 0° C. The reaction mixture is stirred for 3 h and is then poured onto a mixture of water and ice. A saturated aqueous sodium hydrogencarbonate solution and dichloromethane are added. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over sodium sulfate and then the solvent is evaporated under reduced pressure to result in 7.8 g of 3,4-dihydroquinoline-1(2H)-carbonyl chloride.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. washwashed with water and with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customto result in 7.8 g of 3,4-dihydroquinoline-1(2H)-carbonyl chloride

Sources & evidence

ORD record
ord-95da523a6a5c438aa7b2554925e9f812
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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