Hydrazine hydrate (1:1) → 4-(4-Nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one

HRID 600269Notes

Reaction equation

HRID 600269 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[O:11]2)[S:7][CH:8]=1)([O-:3])=[O:2].O.[NH2:21][NH2:22]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:11])[NH:22][N:21]=2)[S:7][CH:8]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 689101193-(4-Nitro-thiophen-2-ylmethylene)-3H-isobenzofuran-1-one

Product 1

HCID 598565794-(4-Nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one

Conditions

Temperature
90 °C

Procedure

A suspension of 3-(4-nitro-thiophen-2-ylmethylene)-3H-isobenzofuran-1-one (26) (1.95 g, 5.17 mmol) in hydrazine monohydrate (0.6 mL, 12.0 mmol) was heated to 90° C. for 1 hour and then cooled to room temperature. The mixture was filtered and the filtered cake was washed with water (3×40 mL), hexane (2×40 mL) and dried in vacuo at 50° C. Two peaks in LC-MS analysis, (1.0 g, 61%) and required no further purification; m/z (LC-MS, ESP), RT=4.05 mins (M+H) 289, & RT=3.71 mins (M+H) 289.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe filtered cake was washed with water (3×40 mL), hexane (2×40 mL)
  4. customdried in vacuo at 50° C
  5. customno further purification

Sources & evidence

ORD record
ord-d3d2d46dceb148539be8aa046292d957
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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