Hydrazine hydrate (1:1) → 1,4-Benzenediamine, N1,N1-bis(4-aminophenyl)-

HRID 418973Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O1CCOCC1.O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 300-mL, 3-necked flask equipped with a reflux tube were added 1.52 g (4.00 mmol) of tri(4-nitrophenyl)amine and 5% Pd/C (200 mg), and the inside was replaced with argon. Dioxane (50 mL) and ethanol (25 mL) were added thereto, and the resulting mixture was stirred at a temperature of 80° C., and hydrazine monohydrate (8.0 mL) was added dropwise thereto over 3 hours and further stirred at 80° C. for 20 hours. The catalyst was separated by filtration, and then the reaction mixture was added to ice water (400 mL). The obtained gray solid was obtained by filtration, washed with water and then vacuum-dried, whereby a desired product was obtained (Quantity: 1.02 g, 3.51 mmol, Yield: 88%).

Workup

customTo a 300-mL, 3-necked flask equipped with a reflux tube
additionwas added dropwise
customThe catalyst was separated by filtration
additionthe reaction mixture was added to ice water (400 mL)
customThe obtained gray solid was obtained by filtration
washwashed with water
customvacuum-dried

Sources & evidence

ORD record: ord-50add8a716234dda9ad96b791434de36
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093349B2

Reaction notes

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