Diethyl Oxalate → HCID 135705332, compound

HRID 442211Notes

Reaction equation

HRID 442211 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:15]([NH2:17])=[O:16])[C:8]([NH2:14])=[N:9]3)=[CH:4][C:3]=2[O:2]1.C[O-].[Na+].[C:21](OCC)(=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]4[C:15](=[O:16])[NH:17][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:14][C:8]4=[N:9]3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 5311899HCID 5311899, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 135705332HCID 135705332, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 6,7-methylenedioxy-2-aminoquinoline-3-carboxamide (1.50 g., 6.5 millimoles), sodium methoxide (0.05 g., 1.25 millimoles) and diethyl oxalate (150 ml.) is heated to 150° C. for 3.5 hours. The mixture is then cooled to room temperature to precipitate the product which is recovered by filtration (1.0 g.). It is purified by chromatography on silica gel using chloroform:methanol (99:1) as eluant. The product is recovered by evaporation of the eluate and recrystallization of the residue from ethanol. Yield = 0.414 g. (20.4%) of the cyclized product. M.P. 267° C. (dec.).

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. customto precipitate the product which
  3. filtrationis recovered by filtration (1.0 g.)
  4. customIt is purified by chromatography on silica gel
  5. customThe product is recovered by evaporation of the eluate and
  6. customrecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-d72648ecedd44c1a88a061de97170eaa
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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