4-Amino-1,3-dihydro-2-benzofuran-1-one → 4-{[2-Hydroxy-4,4-dimethyl-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalide

HRID 1444519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444519
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH3:20])([CH3:19])[CH2:10][C:11]([OH:18])([C:14]([F:17])([F:16])[F:15])[CH:12]=O.[NH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH2:24][O:25][C:26]2=[O:27].Br(Br)(Br)Br>>[CH3:19][C:9]1([CH3:20])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:12]([NH:21][C:22]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:23]=2[CH2:24][O:25][C:26]3=[O:27])[C:11]([OH:18])([C:14]([F:15])([F:17])[F:16])[CH2:10]1

Komponenten

3

Edukt 2

HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 179890984-(2-Methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Produkt 1

HCID 686800504-{[2-Hydroxy-4,4-dimethyl-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalideAusbeute 19 %

Versuchsvorschrift

Analogously to Example 10, the corresponding imine is produced starting from 600 mg of 4-(2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 308 mg of 4-aminophthalide. By reaction of 640 mg of the imine with 7.7 ml of bromine tribromide solution (1 M in dichloromethane), 165 mg of 4-{[4,4-dimethyl-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalide is obtained as fraction 1, and 115 mg of 4-{[2,5-dihydroxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalide is obtained as fraction 2.

Quellen und Nachweise

ORD-Eintrag
ord-4a4b7b2843f24250aa8c7c73ce7e44c7
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662821B2

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