Formic Acid → HCID 23505702, compound

HRID 1884386Notes

Reaction equation

HRID 1884386 reaction equation
C1O[C:16]23[O:17][CH2:18][O:19][C:15]2=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[C:4]([NH2:21])[CH:3]3O1.[CH:22]([OH:24])=[O:23].[CH:25]([NH2:27])=O>>[CH2:18]1[O:17][C:16]2[CH:3]=[C:4]3[C:5]([C:6]([C:8]4[CH:9]=[CH:10][C:11]5[O:23][CH2:22][O:24][C:12]=5[CH:13]=4)=[N:27][CH:25]=[N:21]3)=[CH:14][C:15]=2[O:19]1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 68677198HCID 68677198, compound

Product 1

HCID 23505702HCID 23505702, compound

Procedure

To a suspension of 3,4-(methylenedioxy)-2-amino-4,5-(methylenedioxy)benzophenone (100 mg, 0.32 mmol) in formamide (1.0 mL) was added formic acid (0.5 mL). The resulting mixture was refluxed under argon for 45 min, cooled to rt, poured into ice water (10 mL), and stirred for 30 min. The resulting precipitate was collected by filtration and the solid was dissolved in ethyl acetate. The solution was washed with water and brine, dried over anhydrous MgSO4 and the solvent was removed in vacuo. The crude product was purified by chromatography on silica gel. Elution with hexane:acetone (70:30) gave the title compound (52 mg); mp 180-185° C. 1H NMR (DMSO-d6) 9.05 (s,1H), 7.40 (s, 1H), 7.33 (s,1H), 7.28 (s,1H), 7.23 (d, J=7.98, 1H), 7.10 (d, J=7.98, 1H), 6.25 (s, 2H), 6.10 (s, 2H). Anal. calcd. for C16H10N2O4: C, 65.31; H, 3.43; N, 9.52. Found: C, 65.07; H, 3.59; N, 9.30.

Workup

  1. temperatureThe resulting mixture was refluxed under argon for 45 min
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutionthe solid was dissolved in ethyl acetate
  4. washThe solution was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified by chromatography on silica gel
  8. washElution with hexane:acetone (70:30)

Sources & evidence

ORD record
ord-fba85e01058d44bab7582f1f7601f8dd
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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