Furfurylamine → 2-(2-furylmethyl)-1H-isoindole-1,3(2H)-dione

HRID 1968654Notes

Reaction equation

HRID 1968654 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>CCO>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][N:7]1[C:11](=[O:12])[C:10]2[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 6811Phthalic Anhydride

Product 1

HCID 7582102-(2-furylmethyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Furfurylamine (5.70 mL, 61.8 mmol) and phthalic anhydride (10.0 g, 90.9 mmol) were heated to 120° C. for approximately 45 min. The reaction mixture was cooled to it and then suspended in EtOH. The resulting suspension was filtered to afford the title compound i-1a. 1HNMR (500 MHz, CDCl3): δ 7.88 (dd, 2H, J=3.2, 5.3 Hz), 7.73 (dd, 2H, J=3.0, 5.5 Hz), 6.38 (d, 1H, J=3.2 Hz), 6.32 (m, 1H), 4.88 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to it
  2. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-873e032d071449ea8945c2044024cef3
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

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