Hydrochloric Acid → HCID 59631038, compound
Reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=2)[C:10]([O:12]C)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[CH3:21][NH2:22].C[Al](C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=2)[C:10]([NH:22][CH3:21])=[O:12])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1Participants
Conditions
- Temperature
- 60 °C
Procedure
A stirred solution of 3-(4-morpholinyl)-5-nitro-benzoic acid, methyl ester (Example 86c; 0.53 g, 2 mmol) in toluene (5 mL) under an argon atmosphere, is treated with a mixture of methylamine hydrochloride (0.27 g, 4 mmol), trimethylaluminium (2 mL of a 2 M solution in toluene, 4 mmol) in toluene (5 mL) and heated at 60° C. for 18 h. The cooled mixture is then treated with hydrochloric acid (10 mL of 2 M), stirred for 5 min and then treated with aqueous sodium hydroxide (5 mL of 4 M). The mixture is then treated with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with brine (2×50 mL), dried (MgSO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ethyl acetate to afford the title compound as yellow crystalline solid, m.p. 204-207° C.
Workup
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined extracts are washed with brine (2×50 mL)
- dry with materialdried (MgSO4)
- customthe solvent is evaporated off under reduced pressure
- customto give the crude product which
- customis purified by recrystallisation from ethyl acetate
Sources & evidence
- ORD record
- ord-1aa61a4d83bf4dfc8665d217193d17c0
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07956053B2
Reaction notes
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