N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide → 4,5-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione

HRID 527135Notes

Reaction equation

HRID 527135 reaction equation
[NH2:1][C:2]1[C:3]([NH:25]C(=O)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([OH:23])([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[O:21][CH3:22])[C:5]2=[O:24]>Cl.CO.C(Cl)Cl>[NH2:25][C:3]1[C:2]([NH2:1])=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5](=[O:24])[C:6]([OH:23])([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[O:21][CH3:22])[C:7]2=[O:11]

Participants

5

Reactant 1

HCID 71477133N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 714771354,5-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dioneYield 46.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(5-amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (85 mg, 0.19 mmol) was completely dissolved in 6M HCl (1.4 ml) and methanol (0.1 ml), followed by heating for 40 min at 80. The reaction mixture was diluted with methylene chloride, extracted with 2N NaOH aqueous solution, and the concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (30 mg, 44%).

Workup

  1. temperatureby heating for 40 min at 80
  2. extractionextracted with 2N NaOH aqueous solution
  3. customthe concentrated organic layer was purified

Sources & evidence

ORD record
ord-bb13e9f2e9ff411395a63a5e984908fa
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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