Hydrazine hydrate (1:1) → Methyl 2-fluoro-4-hydrazinocarbonylbenzoate

HRID 1881547Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5](O)=[O:6].O[N:16]1C2C=CC=CC=2N=[N:17]1.Cl.CN(C)CCCN=C=NCC.O.NN>>[F:1][C:2]1[CH:3]=[C:4]([C:5]([NH:16][NH2:17])=[O:6])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

Reactant 4

HCID 24654Hydrazine hydrate (1:1)

HCID 757711-Hydroxybenzotriazole

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 592950871-Methyl 2-fluoro-1,4-benzenedicarboxylate

Product 1

HCID 67050257Methyl 2-fluoro-4-hydrazinocarbonylbenzoateYield 21.5%

Procedure

From 3-fluoro-4-methoxycarbonylbenzoic acid (198 mg, 1 mmol), 1-hydroxybenzotriazole (HOBt) (135 mg, 1 mmol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (WSC) (249 mg, 1.3 mmol) and hydrazine monohydrate (73 μL, 1.5 mmol), 45.6 mg of the desired product was obtained in the same manner as in Reference Synthesis Example 50 as a white solid (yield 22%).

Sources & evidence

ORD record: ord-0259b04eb08c4c2ba07e362de67b12af
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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