Hydrochloric Acid → HCID 86613920, compound

HRID 1811408Notes

Reaction equation

HRID 1811408 reaction equation
Cl.[O:2]1CCO[CH:3]1[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][C:11](=[O:23])[N:12]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[C:17]1([N:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[C:7]([CH:3]=[O:2])[C:8]=3[CH2:9][CH2:10][C:11]2=[O:23])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66597019HCID 66597019, compound

Product 1

HCID 86613920HCID 86613920, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2N Hydrochloric acid (5 ml) was added to a solution of 5-(1,3-dioxolan-2-yl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one (2.60 g) in THF (30 ml), followed by stirring at room temperature overnight. After distilling off THF under reduced pressure, ethyl acetate-water was added, and the resulting mixture was washed (twice with water and once with a saturated sodium chloride solution), dried (MgSO4), and concentrated under reduced pressure. The obtained solid was recrystallized from chloroform-diethyl ether to thereby obtain 1.93 g (yield: 87%) of 1-phenyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a beige powder.

Workup

  1. distillationAfter distilling off THF under reduced pressure, ethyl acetate-water
  2. additionwas added
  3. washthe resulting mixture was washed (twice with water
  4. dry with materialonce with a saturated sodium chloride solution), dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained solid was recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-f0ce0c9c5413432db28f7898164d2129
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

Loading…