Methanone, bis(4-methoxy-3-nitrophenyl)- → 3,3'-diamino-4,4'-dimethoxybenzophenone

HRID 726910Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-])=O)[CH:10]=1)=[O:8])([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[C:7]([C:6]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:4]([NH2:1])[CH:5]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a sealed glass reaction vessel equipped with a stirrer, thermometer and reflux condenser, 84 g (0.253 mol) of the above 3,3'-dinitro-4,4'-dimethoxybenzophenone, 420 g of N,N-dimethylformamide and 2.52 g of 5% palladium/alumina catalyst (N.E. Chemcat Co.) were charged and reacted in a hydrogen atmosphere at 45°~55° C. for 3 hours. After finishing the reaction, the catalyst was filtered. The filtrate was heated to 80° C. and then 1275 g of water was added and cooled to temperature to crystallize the desired product. The precipitated crystals were filtered and recrystallized from isopropylalcohol (IPA) to obtain 27 g (39% yield) of 3,3'-diamino-4,4'-dimethoxybenzophenone as light yellow crystals.

Workup

customTo a sealed glass reaction vessel
customequipped with a stirrer
temperaturethermometer and reflux condenser
customthe reaction
filtrationthe catalyst was filtered
addition1275 g of water was added
temperaturecooled to temperature
customto crystallize the desired product
filtrationThe precipitated crystals were filtered
customrecrystallized from isopropylalcohol (IPA)

Sources & evidence

ORD record: ord-8548a54a23a849c0bd3c951a9ba32e93
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710334

Reaction notes

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