Trimellitic anhydride → 2-[3-(1,3-benzoxazol-2-yl)phenyl]-1,3-dioxoisoindole-5-carboxylic acid

HRID 722469Notes

Reaction equation

HRID 722469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:17]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]2[C:26]([O:28][C:29](=O)[C:19]=2[CH:18]=1)=[O:27]>C(O)(=O)C>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:4]1[CH:3]=[C:2]([N:1]2[C:26](=[O:27])[C:20]3[C:19](=[CH:18][CH:17]=[C:22]([C:23]([OH:25])=[O:24])[CH:21]=3)[C:29]2=[O:28])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11089Trimellitic anhydrideHCID 7209873-Benzooxazol-2-yl-phenylamine

Product 1

HCID 12712212-[3-(1,3-benzoxazol-2-yl)phenyl]-1,3-dioxoisoindole-5-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(3-Aminophenyl)benzoxazole (500 mg, 2.4 mmol) and 1,2,4-benzenetricarboxylic anhydride (546 mg, 2.4 mmol) in acetic acid (25 ml) were heated to reflux overnight. On cooling the precipitate was filtered, washed with acetic acid and dried to give the title compound 710 mg (71%). 1H NMR (CDCl3) δ 8.44(dd, J=1.5, 7.9 Hz, 1H), 8.36(d, J=4.5 Hz, 2H) 8.28(dt, J=1.5, 7.2 Hz, 1H), 8.12(d, J=7.9 Hz, 1H), 7.86–7.39(m, 4H), 7.45(m, 2H). MS 383 m/z (M−H)−.

Workup

  1. temperatureto reflux overnight
  2. temperatureOn cooling the precipitate
  3. filtrationwas filtered
  4. washwashed with acetic acid
  5. customdried

Sources & evidence

ORD record
ord-caaaa36ad42e4ac69b14cdd038e97a64
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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