Ammonia → N-(4-Nitrophenyl)-4-(4-pyridinylamino)benzamide
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11](N)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[N:15]1[CH:20]=CC=CC=1.[N+:21]([C:24]1[CH:32]=[CH:31][C:27](C(Cl)=O)=[CH:26][CH:25]=1)([O-:23])=[O:22].N.[O:34]1CCOCC1>>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([NH:15][C:20](=[O:34])[C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:9][CH:10]=2)=[CH:31][CH:32]=1)([O-:23])=[O:22]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a solution of B4 (10.07 g, 54.37 mmol) in dry pyridine (21.90 mL, 271.82 mmol) was added a solution of 4-nitrobenzoyl chloride (10.09 g, 54.37 mmol) in dry dioxane (100 mL), and the resulting mixture was heated at 50° C. for 2 h. After this time, the reaction mixture was cooled to room temperature and basified by addition of aqueous NH3. The resulting precipitate was collected by filtration to give a first batch of amide B5 (3.47 g, 19%) as an amorphous orange-yellow solid. The filtrate was extracted with EtOAc (×4), and the combined organic extracts were washed with brine, and then evaporated to dryness to give a mixture of B4 and B5 (ca. 1:1 by 1H NMR). Re-treatment of this mixture with 4-nitrobenzoyl chloride at 50° C. for 12 h gave a further 4g of B5; 1H NMR [(CD3)2SO]: δ 6.86 (dd, J=4.82, 1.60 Hz, 2H, ArH), 7.21 (dt, J=9.86, 5.02, 3.00 Hz, 2H, ArH), 7.76 (d, J=8.84, 2H, ArH), 8.18 (m, 4H, ArH), 8.37 (ddd, J=9.23, 4.33, 2.34 Hz, 2H, ArH), 8.73 (s, 1H, ArNHAr), 10.52 (s, 1H, ArC(O)NHAr). LCMS (APCI+): 335 (100%).
Workup
- temperatureAfter this time, the reaction mixture was cooled to room temperature
- filtrationThe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-28fcbb2208a7486a8752da7b69f34b7e
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939546B2
Reaction notes
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