Hydrazine hydrate (1:1) → 4-(4-Aminocyclohexyloxy)benzoic acid ethyl ester

HRID 555378Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].O.NN>C(Cl)(Cl)Cl.C(O)C>[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 7.5 °C

Procedure

To a solution of 4-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester (6.3 g, 16.0 mmol) in CHCl3 (50 mL) and ethanol (60 mL) was added hydrazine hydrate (16.0 g, 320.2 mmol). Stirring was continued at ambient temperature for 2 days. The reaction mixture was then cooled to 5-10° C. and the white precipitate was filtered off. The filtrate was washed with water, dried and the solvent evaporated under vacuum to afford 4.15 g (98%) of 4-(4-amino-cyclohexyloxy)-benzoic acid ethyl ester.

Workup

filtrationthe white precipitate was filtered off
washThe filtrate was washed with water
customdried
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-58ea6859ac654d3c99f40af741ae9cb4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053447B2

Reaction notes

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