Urea → 6-tert-butyl-4H-isoquinoline-1,3-dione

HRID 2236490Notes

Reaction equation

HRID 2236490 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[C:7]([CH2:14][C:15]([OH:17])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:18]C(N)=O>>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:12][CH:13]=1)[C:9](=[O:10])[NH:18][C:15](=[O:17])[CH2:14]2)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1176UreaHCID 426258304-Tert-butyl-2-(carboxymethyl)benzoic acid

Product 1

HCID 426251726-tert-butyl-4H-isoquinoline-1,3-dioneYield 55%

Procedure

4-tert-Butyl-2-carboxymethyl-benzoic acid (90 mg, 0.38 mmol) and urea (45 mg, 0.75 mmol) were grinded and mixed in a round bottle flask, then placed into an oil bath, preheated to 145° C. The flask is kept at this temperature for 1 hour before it is cooled to room temperature. Chromatography of the residue afforded the title compound (45 mg, 55%). MS (ESI): 216.1 (M−1)−1.

Workup

  1. additionmixed in a round bottle flask
  2. customplaced into an oil bath
  3. custompreheated to 145° C

Sources & evidence

ORD record
ord-46929121764047f682afb82580a9e47d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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