2-Chlorotoluene → N-Benzyl-o-toluidine

HRID 412789

反応式

HRID 412789 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 72382-ChlorotolueneHCID 7504BenzylamineHCID 23676156Sodium t-butoxide

生成物 1

HCID 79402N-Benzyl-o-toluidine収率 96.5%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

実験手順

According to the general procedure A, 2-chlorotoluene (66 mg, 0.52 mmol) reacted with benzylamine (68 mg, 0.64 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (60 mg, 0.63 mmol) in toluene at 100° C. for 4 h to give the title compound (99 mg, 96%) as a solid after recrystallization from hexane: 1H-NMR (300 MHz, CDCl3): δ 7.48-7.35 (m, 5H), 7.14 (m, 2H), 6.75 (t, 1H, J=7.2 and 7.5 Hz), 6.68 (d, 1H, J=7.8 Hz), 4.44 (s, 2H), 3.93 (bs, 1H), 2.24 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.01, 139.46, 130.02, 128.62, 127.50, 127.20, 127.12, 121.86, 117.13, 109.93, 48.26, 17.52. GC/MS(EI): m/z 197 (M+), 120, 106. Anal. Calcd for C14H15N: C, 85.24; H, 7.66; N, 7.10. Found: C, 84.98; H, 7.64; N, 7.20.

後処理

  1. customat 100° C.
  2. customfor 4 h

出典と根拠

ORDレコード
ord-c242709ca1684508a1d8e9f3da2adfec
出典データセット
uspto-grants-2003_05
特許番号
US06562989B2

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