Diethyl Oxalate → HCID 53863676, compound

HRID 1065650Notes

Reaction equation

HRID 1065650 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:15])=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][CH3:13])[CH2:8][C:7]2=[O:14].[CH2:16]([O:18][C:19](=[O:25])[C:20](OCC)=[O:21])[CH3:17]>>[CH2:16]([O:18][C:19](=[O:25])[C:20]([NH:15][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:10]2[C:6]=1[C:7](=[O:14])[CH2:8][CH:9]2[CH2:11][CH2:12][CH3:13])=[O:21])[CH3:17]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 53882376HCID 53882376, compound

Product 1

HCID 53863676HCID 53863676, compound

Procedure

A solution of 7.2 g of 7-methyl-3-oxo-1-propyl-4-indanylamine in 34 ml oxalic acid diethyl ester is boiled under reflux for 2 hours and then cooled to room temperature. The reaction mixture is then heated at 90°-100° at 11 mm Hg to remove the excess oxalic acid diethyl ester. The residue is chromatographed on 200 g silica gel to afford the pure title compound which is recrystallised from ether. M.pt. 84°-86°.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is then heated at 90°-100° at 11 mm Hg
  3. customto remove the excess oxalic acid diethyl ester
  4. customThe residue is chromatographed on 200 g silica gel

Sources & evidence

ORD record
ord-3ae45f6f07e84397ae629bcef88f0fd6
Source dataset
uspto-grants-1982_05
Patent number
US04330555

Reaction notes

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