Hydrochloric Acid → 2-[(2,6-Dichloro-3-methylphenyl)amino]benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](C)[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.Cl.[CH3:21]NOC.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>ClCCl.N1C=CC=CC=1>[Cl:9][C:4]1[C:5]([CH3:21])=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[CH:13]=[O:15]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture in dry dichloromethane (135 mL) of 2-[(2,6-dichloro-4-methylphenyl)amino]benzoic acid (meclofenamic acid) (7.0 g, 23.6 mmol), N,O-dimethylhydroxylamine hydrochloride (5.0 g, 51.9 mmol), carbon tetrabromide (17.2 g, 51.9 mmol), triphenylphosphine (13.6 g, 51.9 mmol), and pyridine (10 mL) was stirred at ambient temperature for 48 hours. The reaction mixture was poured into 10% HCl (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo. Purification by chromatography on silica gel (9:1 hexane/ethyl acetate) provided 7.98 g (99%) of 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde as a colorless solid.
Workup
- extractionextracted with ethyl acetate (3×200 mL)
- washThe combined organic layers were washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated in vacuo
- customPurification by chromatography on silica gel (9:1 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-eea4ac23e351495a8deb42c525e825c6
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840758
Reaction notes
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