Urea → 6-bromo-7-methoxy-4H-isoquinoline-1,3-dione

HRID 2236533Notes

Reaction equation

HRID 2236533 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([Br:14])[C:11]([O:15][CH3:16])=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[NH2:17]C(N)=O>O>[Br:14][C:12]1[CH:13]=[C:5]2[C:6](=[CH:10][C:11]=1[O:15][CH3:16])[C:7](=[O:8])[NH:17][C:1](=[O:2])[CH2:4]2

Participants

4

Reactant 2

HCID 1176UreaHCID 592999302-Carboxymethyl-4-bromo-5-methoxy-benzoic acid

Product 1

HCID 593001906-bromo-7-methoxy-4H-isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Carboxymethyl-4-bromo-5-methoxy-benzoic acid (228 mg, 0.785 mmole) and urea (0.110 g, 1.82 mmole) is stirred and heated using an oil bath at 195° C. After one hour the mixture is cooled to room temperature and treated with water, collected by filtration, washed with water and dried to give a brown-black solid, 106 mg, (50%); MS (ES−): m/z 268.1, 270.1 (M−H).

Workup

  1. temperatureheated
  2. customat 195° C
  3. filtrationcollected by filtration
  4. washwashed with water
  5. customdried
  6. customto give a brown-black solid, 106 mg, (50%)

Sources & evidence

ORD record
ord-534fb46d830a4f55a3b83a0f09a1d044
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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