Hydrogen Bromide → 2-Chloro-3,4-dihydroxybenzaldehyde

HRID 2198752ノート

反応式

HRID 2198752 の反応式
[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([O:11]C)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br>>[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

3

反応物 2

HCID 260Hydrogen BromideHCID 603956Chloroisovaniline

生成物 1

HCID 5988142-Chloro-3,4-dihydroxybenzaldehyde

実験手順

2-Chloro-3-hydroxy-4-methoxybenzaldehyde is treated with hydrogen bromide to give 2-chloro-3,4-dihydroxybenzaldehyde which is converted to the methylenedioxy derivative with dibromomethane as described above. The product is condensed with nitromethane and the resulting nitroethylene reduced to give the phenethylamine. This compound is condensed with p-methoxystyrene oxide to give the α-hydroxyphenethylamine intermediate which is treated with an excess of trifluoroacetic acid at room temperature for 18 hours to give 6-chloro-7,8-methylenedioxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine. This compound is split using boron trichloride as described above to give 6-chloro-7,8-dihydroxy-1-p-methoxyphenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

出典と根拠

ORDレコード
ord-e2544613515643ab84cd63000901ec40
出典データセット
uspto-grants-1982_11
特許番号
US04359464

反応ノート

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