Hydrazine hydrate (1:1) → HCID 66597143, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].O.NN>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:16][NH2:17])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
The obtained 2-[(3-nitro-4-phenylphenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione was dissolved in ethanol (30 mL), an aqueous solution of hydrazine monohydrate (2 mL) was added thereto, and the mixture was stirred at 70° C. for 1 hour. The reaction solution was filtered, to the filtrate was added 0.6 M hydrochloric acid and ethyl acetate, and the mixture was stirred vigorously. The aqueous layer was separated and, after being neutralized with a 5M aqueous solution of sodium hydroxide, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain (3-nitro-4-phenylphenyl)methanamine as a crude material (305.5 mg)
Workup
- filtrationThe reaction solution was filtered, to the filtrate
- additionwas added 0.6 M hydrochloric acid and ethyl acetate
- stirringthe mixture was stirred vigorously
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f3b80fee544d44879f8071b7d28f6876
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09072734B2
Reaction notes
Loading…