Phthalic Anhydride → HCID 69800740, compound

HRID 1070532Notes

Reaction equation

HRID 1070532 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[C:12]1([C:18]2[CH2:23][C:22](=[C:24]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[CH:21]=[CH:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 770264-Methyl-2-phenylpyridine

Product 1

HCID 69800740HCID 69800740, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
200 °C

Procedure

Under exclusion of air, a mixture of phthalic anhydride (4.38 g, 29.5 mmol) and 2-phenyl-4-picoline (5.0 g, 29.5 mmol) was heated to 200° C. The reaction melt was stirred at 200° C. for 14 h until a yellow precipitate was formed. The reaction was cooled to 100° C. and ethanol (300 mL) was added. The resultant brown mass was refluxed in ethanol for 1 h and sonicated in a water bath to break up the compound. The precipitate was filtered and triturated in ethanol (100 mL) to give the title compound as a yellow solid (3.2 g, 10.7 mmol, 36% yield). 1H-NMR (DMSO-d6) 12.06 (broad s, 1H), 9.04 (d, J=1.3, 1H), 8.68 (dd, J=6.7, 1.3, 1H), 8.17 (d, J=6.7, 1H), 7.79 (dd, J=8.0, 5.2, 2H), 7.61 to 7.64 (m, 3H), 7.45 to 7.53 (m, 4H); MS ES 300 (M+H)+, calc. 299; TLC (1:2:8 v/v methanol-acetone-dichloromethane) Rf=0.32.

Workup

  1. customwas formed
  2. temperatureThe reaction was cooled to 100° C.
  3. customsonicated in a water bath
  4. filtrationThe precipitate was filtered
  5. customtriturated in ethanol (100 mL)

Sources & evidence

ORD record
ord-955bee2cbbb64e8a8adedfea8ae33baa
Source dataset
uspto-grants-2005_06
Patent number
US06903101B1

Reaction notes

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