2-(1,3-Dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)acetic acid → 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)acetyl chloride

HRID 571345Notes

Reaction equation

HRID 571345 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])[N:3]1[CH2:13][C:14]([OH:16])=O.[Cl:17]C(Cl)OCC>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])[N:3]1[CH2:13][C:14]([Cl:17])=[O:16]

Participants

4

Reactant 2

HCID 5764902-(1,3-Dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)acetic acidHCID 12643245(Dichloromethoxy)ethane

Product 1

HCID 866817622-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)acetyl chlorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)acetic acid (150 mg, 0.684 mmol) in CHCl3 (3 ml), (dichloromethoxy)ethane (1 ml, 0.684 mmol) was added, and the mixture refluxed for 3 hours. The solvent was evaporated under reduced pressure, the crude taken up with CHCl3, and the solvent evaporated again to give the title compound (163 mg, quantitative yield).

Workup

  1. temperaturethe mixture refluxed for 3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe solvent evaporated again

Sources & evidence

ORD record
ord-c1576d2d523a42ceacd924c77dbc08eb
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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