Hydrazine hydrate (1:1) → 3-(7-Chloro-6-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)benzonitrile

HRID 1428931Notes

Reaction equation

HRID 1428931 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:3]=1.O.[NH2:24][NH2:25]>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[NH:24][N:25]=[C:13]2[C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:20]#[N:21])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 904182224-Chloro-2-(3-cyanobenzoyl)-5-methoxybenzoic acid

Product 1

HCID 904173793-(7-Chloro-6-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)benzonitrileYield 20.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-chloro-2-(3-cyanobenzoyl)-5-methoxybenzoic acid (3.0 g, 9.50 mmol) in hydrazine hydrate (0.6 mL 11.4 mmol) and EtOH (40 mL) was heated at 80° C. for 2 h. The reaction mixture was diluted with water (100 mL), and the precipitate was filtered and dried to obtain 3-(7-chloro-6-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)benzonitrile (0.6 g, 17%) (312.4 [M+H]) 1H NMR: (400 MHz, DMSO) δ: 3.96 (s, 3H), 7.64 (s, 1H), 7.79-7.75 (t, 1H), 7.87 (s, 1H), 7.96-7.94 (d, J=8, 1H), 8.04-8.02 (d, J=8, 1H), 8.09 (s, 1H), 13.03 (s, 1H).

Workup

  1. filtrationthe precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-689575ce4a8e4250ad7358b1de5be181
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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