Hydrazine hydrate (1:1) → HCID 90418704, compound

HRID 1428927Notes

Reaction equation

HRID 1428927 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([C:7]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:8]=1[C:9](O)=[O:10])=O.O.[NH2:22][NH2:23]>CCO>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[C:9](=[O:10])[NH:23][N:22]=2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68659330HCID 68659330, compound

Product 1

HCID 90418704HCID 90418704, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-fluorobenzoyl)-5-methoxybenzoic acid (21 g, 76.5 mmol) in hydrazine hydrate (4.09 mL, 84.0 mmol) and EtOH (300 mL) was heated overnight at 80° C. The reaction mixture was concentrated, diluted with water (300 mL), and the precipitate was filtered and dried to yield 4-(3-fluorophenyl)-7-methoxyphthalazin-1(2H)-one (7.2 g). (270.85 [M+H]) 1H NMR: (400 MHz, DMSO) δ: 3.96 (s, 3H), 7.36-7.43 (m, 3H), 7.46-7.49 (m, 1H), 7.57-7.64 (m, 2H), 7.73-7.73 (d, J=2.8, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (300 mL)
  3. filtrationthe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-f091464273ba4053936438a2a49bd541
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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