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

HRID 2236442Notes

Reaction equation

HRID 2236442 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(Cl)(Cl)Cl>[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

4

Reactant 2

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

Product 1

HCID 426251726-tert-butyl-4H-isoquinoline-1,3-dioneYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

An amount of 1.5 g (6.35 mmol) of 4-tert-butyl-2-(carboxymethyl)benzoic acid and urea (763 mg, 12.7 mmol) were heated neat at 145-148° C. for 1.5 hours. The mixture is cooled to room temperature and 200 mL of chloroform is added and washed 3× with water, dried over sodium sulfate and evaporated. The crude product is purified by column chromatography 4% methanol methylene chloride to give 580 mg (41% yield) of the product as a brown solid. MS (ESI) m/z 218.2 (M+1).

Workup

  1. washwashed 3× with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product is purified by column chromatography 4% methanol methylene chloride

Sources & evidence

ORD record
ord-4dfe28ca843945e6942ac8abf44254b5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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