Methanol → 2-[(2,6-Dichloro-3-methylphenyl)amino]benzaldehyde
Reaction equation
CON(C)[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15](C)=[CH:14][C:13]=1[Cl:20].[H-].[CH2:24]([Al+]CC(C)C)C(C)C.CO>C1COCC1>[Cl:18][C:17]1[C:16]([CH3:24])=[CH:15][CH:14]=[C:13]([Cl:20])[C:12]=1[NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]=[O:21]Participants
Procedure
To a magnetically stirred 0° C. solution in dry THF (25 mL) of N-methoxy-N-methyl-2-[(2,6-dichloro-4-methylphenyl)amino]benzamide (3.8 g, 11.2 mmol), prepared as in step 1, was added dropwise diisobutylaluminum hydride (1.0M in THF, 24.6 mL) and the reaction mixture was stirred at ambient temperature for 16 hours. Methanol (5 mL) was added dropwise and the mixture was stirred for 15 minutes until a white precipitate had formed. The reaction mixture was concentrated, the residue was taken up in methanol (10 mL), the insoluble white solid was filtered, and the filtrate was evaporated in vacuo and then purified by chromatography on silica gel (5:1 hexane/CH2Cl2) to provide 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde (1.98 g; 63%) and over reduced alcohol side product (0.70 g; 22%).
Workup
- stirringthe mixture was stirred for 15 minutes until a white precipitate
- customhad formed
- concentrationThe reaction mixture was concentrated
- filtrationthe insoluble white solid was filtered
- customthe filtrate was evaporated in vacuo
- custompurified by chromatography on silica gel (5:1 hexane/CH2Cl2)
Sources & evidence
- ORD record
- ord-569e3f0cf38b4282a44e341e8299339e
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840758
Reaction notes
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