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Dichloromethane → N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

HRID 1352501
ノート
印刷プレビュー

反応式

HRID 1352501 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])=[CH:10][CH:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl>CO.[B-](F)(F)(F)F.COC1C([P@](CC[P@](C2C=CC=CC=2)C2C(OC)=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.C1CC=CCCC=C1.[Rh]>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])[CH2:10][CH:9]1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6344DichloromethaneHCID 22935749N-(1-benzyl-2-methyl-1,2-dihydroquinolin-4-yl)-N-phenylacetamide

生成物 1

HCID 22935741N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide収率 79.6%

試薬・触媒・溶媒 2

HCID 10930696(1Z,5Z)-cycloocta-1,5-diene;(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;rhodium;tetrafluoroborate触媒
HCID 887
Methanol
溶媒

実験手順

A solution of N-(1-benzyl-2-methyl-1,2-dihydroquinolin-4-yl)-N-phenylacetamide (100 mg) and (R,R)-(−)-1,2-bis[(o-methoxyphenyl)(phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium (I) tetrafluoroborate (20 mg) in methanol (6 ml) was stirred under 20 bars of hydrogene overnight. Dichloromethane was added and the organic layer was washed by water and dried over sodium sulfate. The solvent was removed and the mixture was purified by chromatography on silica gel (dichloromethane/ethanol (99:1)) to afford N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (80 mg).

後処理

  1. washthe organic layer was washed by water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed
  4. customthe mixture was purified by chromatography on silica gel (dichloromethane/ethanol (99:1))

出典と根拠

ORDレコード
ord-7a65bf3093904768bfc6c7e4eaf63d2e
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07220760B2

反応ノート

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