Acetic Acid → HCID 10829879, compound

HRID 442668Notes

Reaction equation

HRID 442668 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([C:15](=O)[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=2)[O:2]1.O.[NH2:27][NH2:28].C(O)(=O)C>C(O)C>[CH2:1]1[O:2][C:3]2=[CH:4][C:5]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=4)=[N:28][NH:27][C:11](=[O:12])[CH2:10][C:6]=3[CH:7]=[C:8]2[O:9]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 404213Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate

Product 1

HCID 10829879HCID 10829879, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4,5-methylenedioxy-2-(4-nitrobenzoyl)phenylacetate (90 mg, 0.26 mmol), hydrazine hydrate (50 μL, 0.88 mmol), and acetic acid (40 μL) in ethanol (15 mL) was refluxed for 4 days. A yellow solid precipitated out from the solution. After cooling, the solvent was removed via pipette and the solid was washed with EtOAc (twice) and hexane, dried in vacuo to provide the title compound (40 mg, 47%), mp: 293°-295° C. 1H NMR (DMSO-d6) 11.2 (s, 1H), 8.31(d, 2H, J=8.8), 7.79 (d, 2H, J=8.8), 7.13 (s, 1H), 6.65 (s, 1H), 6.12 (s, 2H), 3.45 (s, 2H). Anal. Calcd. for C16H11N3O5 : C, 59.08; H, 3.41; N, 12.92. Found: C, 59.05; H, 3.43; N, 2.83.

Workup

  1. customA yellow solid precipitated out from the solution
  2. temperatureAfter cooling
  3. customthe solvent was removed via pipette
  4. washthe solid was washed with EtOAc (twice) and hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c9d4305bf88e4e86b8568995907d82c6
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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