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

HRID 535486Notes

Reaction equation

HRID 535486 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11])=O.O.[NH2:19][NH2:20]>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:8]2[C:9](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10](=[O:11])[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11665962HCID 11665962, compound

Product 1

HCID 6865574-thiophen-2-yl-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(thiophene-2-carbonyl)benzoate (0.445 g, 1.81 mmol) and hydrazine hydrate (0.40 mL, 7.1 mmol) in ethanol (6 mL) was stirred at 80° C. overnight, concentrated, and azeotroped with toluene to give the title compound, which was used without purification: 1H NMR (300 MHz, DMSO-d6) δ 12.87 (s, 1H), 8.42-8.28 (m, 1H), 8.23-8.09 (m, 1H), 7.95 (dtd, J=19.0, 7.3, 1.5, 2H), 7.82-7.69 (m, 1H), 7.68-7.55 (m, 1H), 7.33-7.19 (m, 1H), 4.12 (s, OH), 1.91 (s, OH), 1.74 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-d147252f69544594ba75bf50c3562081
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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