Water → 3-Bromo-2-isopropyl-7-(4-methoxybenzylamino)-8-nitro-chromen-4-one

HRID 14486

Reaction equation

HRID 14486 reaction equation
[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([N+:26]([O-:28])=[O:27])[C:7](OS(C3C(C)=CC(C)=CC=3C)(=O)=O)=[CH:8][CH:9]=2)[O:4][C:3]=1[CH:29]([CH3:31])[CH3:30].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([N+:26]([O-:28])=[O:27])[C:7]([NH:39][CH2:38][C:37]3[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)=[CH:8][CH:9]=2)[O:4][C:3]=1[CH:29]([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 866256152,4,6-trimethyl-benzenesulfonic acid 3-bromo-2-isopropyl-8-nitro-4-oxo-4H-chromen-7-yl ester

Product 1

HCID 687031553-Bromo-2-isopropyl-7-(4-methoxybenzylamino)-8-nitro-chromen-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2,4,6-trimethyl-benzenesulfonic acid 3-bromo-2-isopropyl-8-nitro-4-oxo-4H-chromen-7-yl ester (1.906 g, 3.5 mmol) in dry toluene (18 ml) in a 20 ml capacity microwave tube is added p-methoxybenzylamine (0.69 ml, 5.26 mmol). The mixture is heated at 130° C. under microwave irradiation for 90 minutes and then at 140° C. under microwave irradiation for a further 30 minutes. Water (40 ml) is added, and the mixture is extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated. The crude product is purified by chromatography on silica gel using cyclohexane-ethyl acetate (8:1) as eluant. The product-containing fractions are evaporated under reduced pressure, and the residue is triturated with diethyl ether to give a pale yellow solid.

Workup

  1. customat 140° C. under microwave irradiation for a further 30 minutes
  2. extractionthe mixture is extracted with ethyl acetate (3×100 ml)
  3. washwashed with saturated brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by chromatography on silica gel
  8. customThe product-containing fractions are evaporated under reduced pressure
  9. customthe residue is triturated with diethyl ether
  10. customto give a pale yellow solid

Sources & evidence

ORD record
ord-24bdd29273584eb289dff4c68aa8064e
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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