3-Nitrophthalic anhydride → HCID 67417282, compound

HRID 1727438Notes

Reaction equation

HRID 1727438 reaction equation
C(O)(=O)C.[NH2:5][CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=1)[C:7]#[N:8].C([O-])(=O)C.[Na+].[N+:25]([C:28]1[CH:38]=[CH:37][CH:36]=[C:30]2[C:31]([O:33][C:34](=O)[C:29]=12)=[O:32])([O-:27])=[O:26]>C(O)(=O)C.C(Cl)Cl>[N+:25]([C:28]1[CH:38]=[CH:37][CH:36]=[C:30]2[C:29]=1[C:34](=[O:33])[N:5]([CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=1)[C:7]#[N:8])[C:31]2=[O:32])([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 216313-Nitrophthalic anhydrideHCID 517045Sodium AcetateHCID 67418487HCID 67418487, compound

Product 1

HCID 67417282HCID 67417282, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-2-(3-ethoxy-4-methoxyphenyl)ethanenitrile acetate (8.0 g, 28.5 mmol), sodium acetate (2.6 g, 31 mmol) and 3-nitrophthalic anhydride (5.5 g, 28.5 mmol) in glacial acetic acid (60 mL) was heated to reflux for 5 hours. The mixture was concentrated in vacuo to give an oil. The oil was dissolved in CH2Cl2, and washed with water and brine, and dried over MgSO4. Solvent was removed and the residue was purified by chromatography (SiO2, Hexane: EtOAc 6:4) to give 9.5 g (84%) of 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-2-(3-ethoxy-4-methoxyphenyl)ethanenitrile; mp 155-157° C.; 1H NMR(DMSO-d6) δ 8.31 (d, J=7.8 Hz, 1H), 8.20 (d, =7.2 Hz, 1H), 8.09 (t, J=7.8 Hz, 1H), 7.06-6.91 (m, 3H), 5.59 (t, J=8.0 Hz, 1H), 4.04-3.96 (q, J=7 Hz, 2H), 3.74 (s, 3H), 3.66 (d, J=8 Hz, 2H), 1.31 (t, J=7 Hz, 3H); 13C NMR (DMSO-d6) δ 165.46, 162.69, 149.07, 147.78, 144.45, 136.63, 132.81, 128.81, 128.52, 127.24, 122.39, 119.77, 118.08, 112.46, 111.68, 63.80, 55.48, 50.36, 20.30, 14.60. Analy. Calculated For C20H17N3O6: C 60.75; H 4.34; N 10.63. Found: C 60.95; H 4.37; N 10.50.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customto give an oil
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed
  8. customthe residue was purified by chromatography (SiO2, Hexane: EtOAc 6:4)

Sources & evidence

ORD record
ord-2f37f70c49ce439797e7a0639890c1b7
Source dataset
uspto-grants-2009_02
Patent number
US07495112B2

Reaction notes

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