Ethanol → HCID 54322974, compound

HRID 327436

Reaction equation

HRID 327436 reaction equation
[CH:1]([NH:3][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2].[O-]CC.[Na+].C(O)C.Br[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2>>[CH:1]([NH:3][C:4]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2)([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 80617Diethyl formamidomalonateHCID 3469148-(Bromomethyl)quinolineHCID 2723922Sodium ethoxide

Product 1

HCID 54322974HCID 54322974, compoundYield 58%

Procedure

Diethyl (formylamino)malonate (22.0 g, 0.108 mol) was added to a stirred solution of sodium ethoxide in ethanol (prepared from 2.4 g of sodium and 250 mL of ethanol, 0.10 mol). After 5 min, 8-(bromomethyl)quinoline (22.0 g, 0.10 mol) was added and the solution was stirred for an additional 15 minutes. The solvent was removed under reduced pressure and the product was partitioned between ethyl acetate and water. The ethyl acetate was removed and the residual oil was crystallized from ether to give 19.9 g (58%) of diethyl (formylamino)(8-quinolinylmethyl)propanedioate, mp 120°-122° C. Anal. Calcd. for C18H20N2O5 : C, 62.78; H, 5.85; N, 8.14. Found: C, 62.53; H, 6.03; N, 8.07.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was partitioned between ethyl acetate and water
  3. customThe ethyl acetate was removed
  4. customthe residual oil was crystallized from ether

Sources & evidence

ORD record
ord-c7e9f2ae288440aba73aa4f12ce073de
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Linked notes

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