Acetic Acid → HCID 19858390, compound

HRID 2073336Notes

Reaction equation

HRID 2073336 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.C1(C)C=CC=CC=1.O.[C:32](O)(=O)[CH3:33]>C(Cl)Cl>[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:33][C:32]=2[CH:23]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 1140TolueneHCID 2309764-Nitrophthalic acid anhydrideHCID 53748840HCID 53748840, compound

Product 1

HCID 19858390HCID 19858390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-nitro phthalic anhydride (3.57 g, 18.5 mmol) and freshly prepared 4-aminobenzocyclobutene 2.20 g (18.5 mmol) was heated to reflux in acetic acid (100 ml) and toluene (100 ml) under nitrogen. The water of condensation was removed continuously and azeotropically using a Dean-Stark trap. After about 17 hrs, the dark but homogeneous reaction mixture was allowed to cool to room temperature and poured into 600 ml water. The mixture was then extracted with ethyl acetate (100 ml, then 4 ×50 ml). The organic extract was washed with aq. NaHCO3 and then H2O, and finally dried over MgSO4. Immediately after the removal of hydrated MgSO4 by filtration, the filtrate was subjected to rotary evaporation to provide slightly tacky yellow-green crude product, which was redissolved in CH2Cl2. The resultant solution was filtered through a bed of silica gel (approximately 20 g) and washed with CH2Cl2 until the filtrate was colorless. The combined filtrate was again stripped on a rotary evaporator to afford yellow plates, which was collected on a fitted filter funnel, washed with petroleum ether and dried in oven under vacuum at 80° C. overnight. Yield 3.85 g (71%). Calc. for C16H10N2O4 :65.30% C; 3.42% H; 9.52% N. Found: 64.17% C; 3.29% H; 9.54% N. Mass Spectroscopy: M+ (294, 100%).

Workup

  1. temperaturewas heated
  2. customwas removed continuously
  3. additionpoured into 600 ml water
  4. extractionThe mixture was then extracted with ethyl acetate (100 ml
  5. extractionThe organic extract
  6. washwas washed with aq. NaHCO3
  7. dry with materialH2O, and finally dried over MgSO4
  8. customImmediately after the removal of hydrated MgSO4
  9. filtrationby filtration
  10. customthe filtrate was subjected to rotary evaporation
  11. customto provide slightly tacky yellow-green crude product, which
  12. filtrationThe resultant solution was filtered through a bed of silica gel (approximately 20 g)
  13. washwashed with CH2Cl2 until the filtrate
  14. customThe combined filtrate was again stripped on a rotary evaporator
  15. customto afford yellow plates, which
  16. customwas collected on a fitted
  17. filtrationfilter funnel
  18. washwashed with petroleum ether
  19. customdried in oven under vacuum at 80° C. overnight

Sources & evidence

ORD record
ord-9ff2b8aaab8948e6b0d4847fde9cea73
Source dataset
uspto-grants-1990_04
Patent number
US04916235

Reaction notes

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