Hydrazine hydrate (1:1) → HCID 10221329, compound

HRID 442663Notes

Reaction equation

HRID 442663 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]2[O:15][CH2:16][O:17][C:12]2=[CH:11][C:10]=1[CH2:18][C:19]([O:21]C)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:24][NH2:25]>C(O)C>[CH2:16]1[O:15][C:13]2=[CH:14][C:9]3[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:25][NH:24][C:19](=[O:21])[CH2:18][C:10]=3[CH:11]=[C:12]2[O:17]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4069581,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester

Product 1

HCID 10221329HCID 10221329, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-benzoyl-4,5-methylenedioxyphenylacetate (110 mg, 0.37 mmol) and hydrazine hydrate (30 μL, 0.53 mmol) in ethanol (15 mL) was refluxed for 5 days. The solvent was removed in vacuo and the resulting residue was separated by chromatography to yield the title compound (30 mg, 0.11 mmol, 29%), mp, 182°-184° C. 1H NMR (CDCl3) 8.59 (s, 1H), 7.60-7.41 (m, 5H), 6.83 (s, 1H), 6.63 (s, 1H), 6.03 (s, 2H), 3.46 (s, 2H). Anal. Calcd. for C16H12N2O3.0.25H2O: C, 67.48; H, 4.42; N, 9.84. Found C, 67.25; H, 4.21; N, 9.88.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was separated by chromatography

Sources & evidence

ORD record
ord-609c3bbbf5b54524ae40ef350c45255c
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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