4,5-Dimethoxyanthranilic acid → 6,7-Dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 557124Notes

Reaction equation

HRID 557124 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH3:14][O:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:2]2[NH:1][C:16](=[O:18])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 797364,5-Dimethoxyanthranilic acidHCID 94429Triphosgene

Product 1

HCID 27584236,7-Dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (50.7 mmol) 2-Amino-4,5-dimethoxy-benzoic acid were dissolved in 150 ml tetrahydrofuran. 6.52 g (22.0 mmol) triphosgene were added and the solution was boiled for 3 h. After equilibration to room temperature the reaction mixture was poured on a water/ice mixture. The residue was filtrated and rinsed with methanol.

Workup

  1. filtrationThe residue was filtrated
  2. washrinsed with methanol

Sources & evidence

ORD record
ord-839ff413a2ad4014abdf2d3f04d355f3
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Reaction notes

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