Urea → 1,3(2H,4H)-Isoquinolinedione, 6-fluoro-

HRID 2236519Notes

Reaction equation

HRID 2236519 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[NH2:15]C(N)=O>>[F:14][C:12]1[CH:13]=[C:5]2[C:6](=[CH:10][CH:11]=1)[C:7](=[O:8])[NH:15][C:1](=[O:2])[CH2:4]2

Participants

3

Reactant 2

HCID 1176UreaHCID 3453952-(carboxymethyl)-4-fluorobenzoic acid

Product 1

HCID 120233191,3(2H,4H)-Isoquinolinedione, 6-fluoro-Yield 96.7%

Procedure

An amount of 200 mg (1.01 mmol) of 2-carboxymethyl-4-fluoro-benzoic acid and urea (72.47 mg, 1.22 mmol) were heated neat at 180-190° C. for 45 min. The mixture is cooled to room temperature followed by recrystallization from water and anhydrous ether to give 175 mg (80% yield) of brown solid. MS (ESI) m/z 179.15 (M+1).

Workup

  1. customfollowed by recrystallization from water and anhydrous ether

Sources & evidence

ORD record
ord-91ba81ac32864b8c88c6295a73af49ad
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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