Diisopropylamine → N,N-Diphenyl-N'-(2-chlorophenyl)hydrazine
Reaction equation
Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.CC([O-])(C)C.[Na+].C(NC(C)C)(C)C>CC(O)=O.CC(O)=O.[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:9][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
1,1-Diphenylhydrazine hydrochloride (1.2 equiv., 0.6 mmol, 135 mg), 2-chlorobromobenzene (1.0 equiv., 0.5 mmol, 0.06 mL), Pd(OAC)2 (0.05 equiv, 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), and NaOtBu (1.4 equiv., 0.7 mmol, 67 mg) and diisopropylamine (2 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.) and then heated to 80° C. for 5 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (2% EtOAc/Hex) to give the title product as a white solid (109 mg, 0.37 mmol, 74% yield).
Workup
- customdried test tube which
- customwas capped with a septum
- custompurged briefly with argon (˜1 min.)
- temperatureThe reaction was then cooled to room temperature
- additiondiluted with Et2O (2 mL)
- filtrationfiltered through Celite
- concentrationconcentrated under vacuum
- customThe crude mixture was purified by flash column chromatography (2% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-1ad8f40cc69349b58e774d48ed8588c1
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06465693B2
Reaction notes
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