Hydrochloric Acid → HCID 15924279, compound

HRID 974254Notes

Reaction equation

HRID 974254 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH2:4][CH2:3][C:2]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].Cl>CN(C)C=O>[C:21]([CH2:20][N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH2:4][CH2:3][C:2]1=[O:12])([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 2936414,6,7,8-Tetrahydro-2,5(1H,3H)-quinolinedione

Product 1

HCID 15924279HCID 15924279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.17 g (0.019 mol) of 3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinedione are dissolved in 25 ml of dimethylformamide, mixed with 5.3 g (1.2×0.019 mol) of anhydrous. potassium carbonate and then with 3.52 g (2×0.019 mol) of methyl bromoacetate and the mixture is stirred for 16 hours at ambient temperature. The mixture is neutralised with methanolic hydrochloric acid and evaporated down in a rotary evaporator. The residue is purified by column chromatography (silica gel, eluant: cyclohexane/ethyl acetate (1:1)).

Workup

  1. additionmixed with 5.3 g (1.2×0.019 mol) of anhydrous
  2. customevaporated down in a rotary evaporator
  3. customThe residue is purified by column chromatography (silica gel, eluant: cyclohexane/ethyl acetate (1:1))

Sources & evidence

ORD record
ord-4a061d388f6145d6ab3f4ebeceebf69d
Source dataset
uspto-grants-1991_11
Patent number
US05068334

Reaction notes

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