Acetic Acid → HCID 19858390, compound

HRID 653171Notes

Reaction equation

HRID 653171 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[NH2:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:18]2CC[C:17]=12.O.[C:25](O)(=O)[CH3:26]>>[CH:22]1[C:21]2[CH:18]=[CH:17][C:16]([N:15]3[C:11](=[O:12])[C:6]4=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[C:7]4[C:8]3=[O:10])=[CH:26][C:25]=2[CH:23]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2309764-Nitrophthalic acid anhydrideHCID 53748840HCID 53748840, compound

Product 1

HCID 19858390HCID 19858390, compound

Procedure

A mixture of 4-nitrophthalic anhydride (3.46 g, 17.9 mmol) and 4-aminobenzocyclobutene (2.20g, 18.5 mmol) was refluxed in acetic acid under N2 for about 17 hours. The dark reaction mixture was then allowed to cool to room temperature and poured into 500 ml of H2O, followed by extraction with CH2Cl2 (75 ml+3×50 ml). The dark extract was then washed with approximately 300 ml of H2O and then dried over MgSO4. Complete removal of CH2Cl2 from the extract by rotary evaporator afforded a dark oil, which was purified by column chromatography (150 g silica gel; using 1:1 petroleum ether/CH2Cl2 as eluent). Pure product was isolated from the first fraction as yellow solid. Yield: 3.21 g (65%). Calc. for C16H10N2O4 : 65.30% C; 3.42% H; 9.52% N. Found: 65.21% C; 3.39% H; 9.58% N. Mass spectroscopy: 294 (M+, 100%). Proton NMR (CDCl3): 3.24 (singlet, alicyclic protons). 7.00-7.23, 8.06-8.72 (complex, aromatic protons). IR(KBr): 2900 w, 2770 m, 2650 m (alicyclic C--H stretches); 1720, 1775 (Symmetric and asymmetric stretches of imide group): 1350, 1540 (symmetric and asymmetric stretches of nitro group).

Workup

  1. customThe dark reaction mixture
  2. extractionfollowed by extraction with CH2Cl2 (75 ml+3×50 ml)
  3. extractionThe dark extract
  4. washwas then washed with approximately 300 ml of H2O
  5. dry with materialdried over MgSO4
  6. customremoval of CH2Cl2 from the
  7. extractionextract by rotary evaporator
  8. customafforded a dark oil, which
  9. customwas purified by column chromatography (150 g silica gel; using 1:1 petroleum ether/CH2Cl2 as eluent)
  10. customPure product was isolated from the first fraction as yellow solid

Sources & evidence

ORD record
ord-352d65e3823444c49c1236b3af3d5351
Source dataset
uspto-grants-1987_06
Patent number
US04675370

Reaction notes

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