Methyl Anthranilate → Benzoic acid, 2-amino-, hydrazide

HRID 1156091Notes

Reaction equation

[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH2:12][NH2:13]>>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:12][NH2:13])=[O:10]

Participants

Reactant 2

HCID 8635Methyl Anthranilate

HCID 9321Hydrazine

Product 1

HCID 94728Benzoic acid, 2-amino-, hydrazide

Procedure

The intermediate o-aminobenzhydrazide is prepared by refluxing 151 g (1.0 mol) methyl anthranilate and 55 g (1.1 mol) 64% aqueous hydrazine in a 250 ml round bottom flask for 2 hours. The product is recrystallized from 1.0 liter ethyl alcohol yielding 75 g of a light yellow solid, melting at 119°-121° C.

Workup

customThe product is recrystallized from 1.0 liter ethyl alcohol yielding 75 g of a light yellow solid, melting at 119°-121° C.

Sources & evidence

ORD record: ord-62c724e87007435d9d08172d27a13336
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04334015

Reaction notes

Loading…