4-Aminobenzoic Acid → HCID 90410908, compound

HRID 1465678Notes

Reaction equation

HRID 1465678 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, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
5 °C

Procedure

About 70 g of 4-amino benzoic acid and 22 g of lithium hydroxide were mixed in 800 mL of DMAc. Then 100 g of 3,5-dibromo-6H-anthra[1,9-cd]isoxazol-6-one was dissolved in the pre-mixed solution. Nitrogen protection was applied to the reaction mixture at 45-55° C. for about 18-20 hours. After reaction completion was confirmed by HPLC, 30 mL of MTBE was slowly added to the reactor. Reaction mixture was then slowly cooled to 0-10° C. under nitrogen protection. Centrifuged the solid and washed with 18 mL of MTBE. Dried the wet cake under 25-30° C. to obtain about 69 g of 4-((3-bromo-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid.

Workup

  1. customAfter reaction completion
  2. additionwas slowly added to the reactor
  3. customReaction mixture
  4. washwashed with 18 mL of MTBE
  5. customDried the wet cake under 25-30° C.

Sources & evidence

ORD record
ord-5401a16b629847748d2f91af23bd3e36
Source dataset
uspto-grants-2015_04
Patent number
US08999992B2

Reaction notes

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