1,2-Difluoro-3-nitrobenzene → HCID 67992187, compound

HRID 467550Notes

Reaction equation

HRID 467550 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:12]1[CH2:21][CH2:20][CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[N:12]1[CH2:21][CH2:20][CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 813351,2-Difluoro-3-nitrobenzeneHCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotate

Product 1

HCID 67992187HCID 67992187, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of difluoronitrobenzene (0.34 mL, 3.10 mmol), methyl isonipecotate (0.51 mL, 3.78 mmol), and diisopropylethylamine (1.08 mL, 6.20 mmol) in acetonitrile (15 mL) was heated at 80° C. overnight. The solvents were removed in vacuo. Chromatographic purification (20% ethyl acetate:hexane) of the residue gave Int-20a (0.85 g, 97%) as a yellow oil.

Workup

  1. customThe solvents were removed in vacuo
  2. customChromatographic purification (20% ethyl acetate:hexane) of the residue
  3. customgave Int-20a (0.85 g, 97%) as a yellow oil

Sources & evidence

ORD record
ord-f052e75235c445878ce3863ad0bd6a0f
Source dataset
uspto-grants-2014_01
Patent number
US08623857B2

Reaction notes

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