N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide → 4,7-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione

HRID 527134Notes

Reaction equation

HRID 527134 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:25]C(=O)C)=[C:6]2[C:10]=1[C:9](=[O:11])[C:8]([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:24]>Cl.CO.C(Cl)Cl>[NH2:25][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[C:10]2[C:6]=1[C:7](=[O:24])[C:8]([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:9]2=[O:11]

Participants

5

Reactant 1

HCID 71477132N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 714771344,7-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dioneYield 235%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(7-amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (45 mg, 0.10 mmol) was completely dissolved in 6M HCl (1.4 ml) and methanol (0.1 ml), followed by heating for 90 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 (80 mg, 200%).

Workup

  1. temperatureby heating for 90 min at 80
  2. extractionextracted with 2N NaOH aqueous solution
  3. customthe concentrated organic layer was purified

Sources & evidence

ORD record
ord-b1918abc3a054959a6cb0e6ea34f8db0
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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