4-Aminobenzoic Acid → HCID 90410908, compound

HRID 527105Notes

Reaction equation

HRID 527105 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Li+].[Br:13][C:14]1[C:27]2=[N:28][O:29][C:25]3=[C:26]2[C:17]([C:18](=[O:30])[C:19]2[C:24]3=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:16](Br)[CH:15]=1.CC(OC)(C)C>CC(N(C)C)=O>[Br:13][C:14]1[C:27]2=[N:28][O:29][C:25]3=[C:26]2[C:17]([C:18](=[O:30])[C:19]2[C:24]3=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:16]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 3939Lithium HydroxideHCID 15413tert-Butyl methyl etherHCID 1115345HCID 1115345, compound

Product 1

HCID 90410908HCID 90410908, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Mixing 4-amino benzoic acid and lithium hydroxide in DMAc, then adding 3,5-dibromo-6H-anthra[1,9-cd]isoxazol-6-one into the mixture at about 40-60° C. Stirring the reaction mixture for up to 24 hours. Adding MTBE to the reaction mixture. Filtering the solid and drying to get 4-((3-bromo-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid (Intermediate 5).

Workup

  1. customat about 40-60° C
  2. filtrationFiltering the solid
  3. customdrying

Sources & evidence

ORD record
ord-2611595dcb014b31adcf5f55e19e95c5
Source dataset
uspto-grants-2016_05
Patent number
US09346788B2

Reaction notes

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