Phthalic Anhydride → Hydrazine

HRID 2181382Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][N:9]=2)=[CH:3][CH:2]=1.C1(=O)OC(=[O:23])C2=CC=CC=C12.CC1C=CN=CC=1>>[CH:15]1[CH:16]=[C:17]2[C:8]([C:7]([C:11](=[O:18])[C:12]2=[CH:13][CH:14]=1)=[C:4]1[CH:5]=[CH:6][NH:1][CH:2]=[CH:3]1)=[O:23].[NH2:9][NH2:10]

Participants

Reactant 3

HCID 6811Phthalic Anhydride

HCID 79634-Methylpyridine

HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

Product 2

HCID 9321Hydrazine

HCID 178515374HCID 178515374, compound

Procedure

The production of, for example, 4-(4-pyridylmethyl)-1(2H)-phthalazinone is carried out according to previously known methods by the reaction of phthalic acid anhydride and 4-methylpyridine at about 200° C. and subsequent reaction of the condensation product that is obtained (γ-pyrophthalone) with excess hydrazine at 130° C. (DE AS 1 061 788). Drawbacks of these methods are the low yield (<50%), low product quality and primarily the necessarily very high temperature of the condensation reaction, which makes very difficult an industrial-scale application of the methods.

Workup

customsubsequent reaction of the condensation product that

Sources & evidence

ORD record: ord-2eb5a019159344d081d265e2a8106834
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06891041B2

Reaction notes

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