Dichloromethane → HCID 59447961, compound

HRID 1916291Notes

Reaction equation

HRID 1916291 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:16]#[N:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([N+:18]([O-])=O)[CH:5]=1.ClCCl>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([NH2:17])[NH:18]2)=[CH:8][CH:9]=1)=[O:21]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 13704246HCID 13704246, compound

Product 1

HCID 59447961HCID 59447961, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Zinc powder (4.9 g) was added portion-wise at 80° C. to a solution of 4-(cyano-ethoxycarbonyl-methyl)-3-nitro-benzoic acid methyl ester (4.40 g, 15 mmol) in acetic acid. The mixture was then heated for 3 hours at 95° C. and 3 hours at 100° C. before being allowed to cool to room temperature at which point the reaction mixture was filtered and the insoluble matter rinsed with acetic acid. The filtrate was concentrated to give a brown oil which was subjected to flash silica chromatography using ethyl acetate as eluent. The partially purified oil was taken up into dichloromethane and the product precipitated using hexane to give the title compound as a pale brown solid (1.71 g, 6.5 mmol). LC-MS (1) Rt 1.88 min; m/z 263.

Workup

  1. temperatureto cool to room temperature at which
  2. filtrationwas filtered
  3. washthe insoluble matter rinsed with acetic acid
  4. concentrationThe filtrate was concentrated
  5. customto give a brown oil which
  6. customthe product precipitated

Sources & evidence

ORD record
ord-24415a0484bc44308ce62fca53a818b5
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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