Hydrochloric Acid → Nitro-(3-oxo-1H,3H-benzo[de]isochromen-1-yl)-acetic Acid Methyl Ester

HRID 660579Notes

Reaction equation

HRID 660579 reaction equation
CO[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH:15]=[O:16])[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:17][O:18][C:19](=[O:24])[CH2:20][N+:21]([O-:23])=[O:22].C(OCC)(=O)C.Cl>CCO.N1CCCCC1>[CH3:17][O:18][C:19](=[O:24])[CH:20]([N+:21]([O-:23])=[O:22])[CH:15]1[C:13]2[C:14]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[C:3](=[O:4])[O:16]1)[CH:10]=[CH:11][CH:12]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 17206Methyl 2-nitroacetateHCID 349031Methyl 8-formylnaphthalene-1-carboxylate

Product 1

HCID 86632579Nitro-(3-oxo-1H,3H-benzo[de]isochromen-1-yl)-acetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8-formylnaphthalene-1-carboxylic acid methyl ester (2.5 g, 11.68 mmol) in EtOH (20 mL) is added 8 drops of piperidine followed by nitroacetic acid methyl ester (2.78 g, 23.4 mmol) and the mixture is stirred at RT for 20 h. Ethyl acetate is added followed by 1N HCl. The resulting precipitate is filtered to give the title compound.

Workup

  1. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-9c1c9066a5de4d7fb35bfb62bd785215
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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