Hexylamine → 2,6-Dimethyl-N-(n-hexyl)aniline

HRID 412782

反応式

HRID 412782 の反応式
Cl[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[NH:16][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参加物

6

反応物 3

HCID 8102HexylamineHCID 328851-Chloro-2,6-dimethylbenzeneHCID 23676156Sodium t-butoxide

生成物 1

HCID 109874092,6-Dimethyl-N-(n-hexyl)aniline収率 97.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

According to the general procedure B, 2-Chloro-m-xylene (70 mg, 0.50 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 2 mol % of Pd(OAc)2, 4 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene (1.5 ml) at 100° C. to give the title compound (100 mg, 97%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.02 (d, 2H, J=7.2 Hz), 6.83 (t, 1H, J=7.2 Hz), 3.00 (t, 2H, J=7.2 and 7.6 Hz), 3.0 (bs, 1H), 2.32 (s, 6H), 1.61 (m, 2H), 1.45-1.31 (m, 6H), 0.93 (t, 3H, J=5.6 and 7.2 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.37, 129.05, 128.75, 121.52, 48.69, 31.73, 31.14, 26.83, 22.62, 18.54, 14.03. GC/MS(EI): m/z 205 (M+).

後処理

  1. customat 100° C.

出典と根拠

ORDレコード
ord-14070a66a4f340c6b271be5fb85b9f58
出典データセット
uspto-grants-2003_05
特許番号
US06562989B2

関連ノート

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