Aniline → HCID 57733276, compound
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]([C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O)[C:7](=O)[CH3:8])=[O:5])[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12](=[O:14])[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]=1[CH3:8])=[O:5])[CH3:2]Participants
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2-(1-ethoxycarbonyl-2-oxo-propyl)-benzoic acid (7.6 g, 30.4 mmol) and aniline (10 ml, 108 mmol) was flushed with argon, sealed in the Emrys process vial and heated at 150° C. for 15 min under microwave irradiation. The volatiles were removed in vacuo and the obtained residue was partitioned between ethyl acetate (100 ml) and 2M HCl (100 ml). The organic layer was washed with brine (2×20 ml), dried (Na2SO4) and evaporated to give 8.7 g of brown oil that solidified. The obtained crude product was of ca. 90% purity according to 1H NMR and can be used in the next step without further purification. Alternatively, the crude product was dissolved in hot ethyl acetate (20 ml), precipitated with heptane (60 ml), allowed to cool, filtered and washed with diethyl ether to give 4.2 g of a pale-brown crystalline solid, yield 45%. LC-MS (m/z) 308.2 (MH+); tR=1.43. 1H NMR (500 MHz, DMSO-d6): 1.34 (t, 3H), 1.97 (s, 3H), 4.41 (q, 2H), 7.38 (d, 2H), 7.51 (t, 1H), 7.56 (t (overlapping m), 3H), 7.62 (d, 1H), 7.8 (t, 1H), 8.22 (d, 1H).
Workup
- customwas flushed with argon
- customsealed in the Emrys process vial
- customThe volatiles were removed in vacuo
- customthe obtained residue was partitioned between ethyl acetate (100 ml) and 2M HCl (100 ml)
- washThe organic layer was washed with brine (2×20 ml)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-cee4c566cb6f4c939f45f21a85c02ac6
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173639B2
Reaction notes
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