Hydrochloric Acid → 7,8-Diamino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

HRID 14489

Reaction equation

HRID 14489 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]2[C:5]([C:6](=[O:25])[C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:8]([CH:15]([CH3:17])[CH3:16])[O:9]2)=[CH:4][CH:3]=1.Cl>CO.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6](=[O:25])[C:7]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)=[C:8]([CH:15]([CH3:16])[CH3:17])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 597242787-Amino-3-(4-chlorophenyl)-2-isopropyl-8-nitro-chromen-4-one

Product 1

HCID 687024427,8-Diamino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Amino-3-(4-chlorophenyl)-2-isopropyl-8-nitro-chromen-4-one (450 mg, 0.94 mmol) is suspended in methanol (5 ml). Concentrated hydrochloric acid (5 ml) is added. The mixture is placed under an atmosphere of argon, and 10% palladium on activated carbon (50 mg) is added. The reaction mixture is placed under an atmosphere of hydrogen and stirred at room temperature for 24 h. The mixture is filtered through a Celite pad, and the Celite pad is washed with methanol (3×30 ml). The filtrate and the washings are combined and evaporated to give a yellow solid.

Workup

  1. filtrationThe mixture is filtered through a Celite pad
  2. washthe Celite pad is washed with methanol (3×30 ml)
  3. customevaporated
  4. customto give a yellow solid

Sources & evidence

ORD record
ord-0189d225b5614d789f5d04eee4b24eaf
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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