Benzyl Alcohol → HCID 20194697, compound

HRID 653431Notes

Reaction equation

HRID 653431 reaction equation
[CH2:1]1[C:10]2=[CH:11][CH:12]=[CH:13][C:8]3=[C:9]2[N:4]([C:5](=[O:14])[CH2:6][CH2:7]3)[C:3](=[O:15])[CH2:2]1.Cl.[C:17]1([CH2:23][OH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:17]1([CH2:23][O:24][C:3](=[O:15])[CH2:2][CH2:1][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]3[C:9]=2[NH:4][C:5](=[O:14])[CH2:6][CH2:7]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 13519806HCID 13519806, compound

Product 1

HCID 20194697HCID 20194697, compound

Procedure

A solution of 1,2,6,7-tetrahydro-3H,5H-benzo[ij]-quinolizine-3,5-dione (20.1 g, 0.1 mole) in phenylmethanol (200 ml) is treated with a drop of concentrated hydrochloric acid. The mixture is refluxed 24 hours (or until the starting dione can no longer be detected by thin layer chromatography). The solution is cooled and concentrated at reduced pressure. The product is purified by flash chromatography to yield 1,2,3,4-tetrahydro-2-oxo-8-quinoline propanoic acid phenylmethyl ester.

Workup

  1. temperatureThe mixture is refluxed 24 hours (or until the starting dione
  2. temperatureThe solution is cooled
  3. concentrationconcentrated at reduced pressure
  4. customThe product is purified by flash chromatography

Sources & evidence

ORD record
ord-846f941e5d60449dbdb53eae21814fae
Source dataset
uspto-grants-1987_06
Patent number
US04677112

Reaction notes

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