1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-[4-(4-Methoxy-5,6,7,8-tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

HRID 1624307

反応式

HRID 1624307 の反応式
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH2:25][CH2:26][CH2:27][CH:28]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:13][O:12][C:7]1[C:6]2[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][CH2:28][CH2:27][CH2:26][CH2:25][N:16]3[C:17](=[O:24])[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:15]3=[O:14])[C:11]=2[N:10]=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 220186174-Methoxy-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 691787902-[4-(4-Methoxy-5,6,7,8-tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione収率 54.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Using General Procedure B: Reaction of 8-amino-4-methoxy-5,6,7,8-tetrahydroquinoline (0.297 g, 1.67 mmol) and 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (0.371, 1.71 mmol) with NaBH(OAc)3 (0.493 g, 2.33 mmol) in CH2Cl2 (8 mL) for 60 minutes followed by purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH3OH) provided 0.345 g (54%) of 2-[4-(4-Methoxy-5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione as an off-white solid.

後処理

  1. customfollowed by purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2—CH3OH)

出典と根拠

ORDレコード
ord-0840b44d153f49e0ae56d128557489e8
出典データセット
uspto-grants-2014_07
特許番号
US08778967B2

関連ノート

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