Benzylamine → N-benzyl-4-methylaniline

HRID 412786ノート

反応式

HRID 412786 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

参加物

6

反応物 3

HCID 7504BenzylamineHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

生成物 1

HCID 79403N-benzyl-4-methylaniline収率 95%

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 A, 4-chlorotoluene (128 mg, 1.01 mmol) reacted with benzylamine (128 mg, 1.19 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (122 mg, 1.27 mmol) in toluene at 100° C. to give the title compound (189 mg, 95%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.43-7.38 (m, 4H), 7.34-7.30 (m, 1H), 7.04 (d, 2H, J=8.26 Hz), 6.61 (d, 2H, J=8.37 Hz), 4.35 (s, 2H), 3.95 (bs, 1H), 2.29 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 145.85, 139.59, 129.70, 128.55, 127.45, 127.10, 126.68, 112.93, 48.56, 20.37. GC/MS(EI): m/z 197 (M+). Anal. Calcd for C14H15N. C, 85.24; H, 7.66; N, 7.10. Found C, 85.29; H, 7.68; N, 7.14.

後処理

  1. customat 100° C.

出典と根拠

ORDレコード
ord-cbbf817f577c42729eb735f5449e5010
出典データセット
uspto-grants-2003_05
特許番号
US06562989B2

反応ノート

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