Sodium Hydroxide → 1-Oxo-1,3-dihydroisobenzofuran-6-carbaldehyde oxime
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=O)[CH:9]=2)[CH2:4][O:3]1.Cl.[NH2:14][OH:15].[OH-].[Na+]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[N:14][OH:15])[CH:9]=2)[CH2:4][O:3]1Participants
Procedure
According to a similar procedure to that described in Example 4-(4), 1-oxo-1,3-dihydroisobenzofuran-6-carbaldehyde (2.42 g, 14.9 mmol) obtained from Example 5-(1), hydroxylamine hydrochloride (1.35 g, 19.4 mmol), and an aqueous solution of sodium hydroxide (1.0N; 19.3 ml, 19.3 mmol) were reacted, and the reaction mixture was worked up to afford 1-oxo-1,3-dihydroisobenzofuran-6-carbaldehyde oxime as a crude solid. According to a similar procedure to that described in Example 4-(4), the crude product obtained above, triethylamine (3.92 g, 39 mmol), and anhydrous trifluoroacetic acid (4.08 g, 19.4 mmol) were reacted, and the reaction mixture was worked up to afford, after extraction and concentration, a solid residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:dichloromethane=0:1˜1:10) to afford the title compound (1.67 g, 70% yield) as a solid (mp. 195-196° C.).
Sources & evidence
- ORD record
- ord-adc1702eb8084071b5b7ded78bea7cb5
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230023B2
Reaction notes
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