Palladium-catalysed ortho arylation of acetanilides
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22⋅79, 21⋅05; IR (KBr plate, CDCl3, cm ) ν = 3275, 21⋅40, 19⋅69, 19⋅14; IR (KBr plate, CDCl3, cm )
3023, 1658, 1523; MS (EI): m/z = 301, 259. Anal. ν = 3271, 3022, 1665, 1522; MS (EI): m/z = 253,
Calcd. for C21H19NO: C, 83⋅69; H, 6⋅35; N, 4⋅65. 211. Anal. Calcd. for C17H19NO: C, 80⋅60; H, 7⋅56;
Found: C, 83⋅85 H, 6⋅19; N, 4⋅74.
N, 5⋅53. Found: C, 68⋅49; H, 7⋅43; N, 5⋅62.
2.1j N-(3-Methoxy-4'-methyl-biphenyl-2-yl)-aceta-
2.1n N-(3′-Methyl-biphenyl-2-yl)-acetamide (3fc):
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mide (3hb): White solid; m.p.: 124–125°C; H White solid; H NMR (300 MHz, CDCl3): δ = 8⋅27
NMR (300 MHz, CDCl3): δ = 7⋅26–7⋅18 (m, 5H), (d, J = 7⋅20 Hz, 1H, NH), 7⋅39–7⋅33 (m, 2H), 7⋅26–
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6⋅93 (d, J = 8⋅40 Hz, 2H), 6⋅66 (s, 1H, NH), 3⋅87 (s, 7⋅18 (m, 6H), 2⋅41 (s, 3H), 2⋅01 (s, 3H); C NMR
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3H), 2⋅40 (s, 3H), 2⋅00 (s, 2H), 1⋅68 (s, 1 H);
C
(75 MHz, CDCl3): δ = 168⋅19, 138⋅89, 138⋅04, 134⋅68,
NMR (75 MHz, CDCl3): δ = 169⋅50, 155⋅09, 140⋅91, 132,18 131⋅78, 129⋅97, 128⋅87, 128⋅66,128⋅27,
136⋅94, 136⋅45, 128⋅90, 128⋅44, 128⋅00, 122⋅83, 126⋅10, 124⋅21, 121⋅43, 24⋅59, 21⋅43; IR (KBr plate,
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122⋅38, 110⋅29, 55⋅87, 23⋅14, 21⋅12; IR (KBr plate, CDCl3, cm ) ν = 3291, 3033, 1687, 1520; MS (EI):
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CDCl3, cm ) ν = 3254, 2955, 1665, 1519; MS (EI): m/z = 225, 183. Anal. Calcd. for C15H15NO: C, 79⋅97;
m/z = 255, 213. Anal. Calcd. for C16H17NO2: C, H, 6⋅71; N, 6⋅22. Found: C, 80⋅13; H, 6⋅58; N, 6⋅40.
75⋅27; H, 6⋅71; N, 5⋅49. Found: C, 75⋅19; H, 6⋅88;
N, 5⋅63.
2.1o N-Acetyl-2,6-di-(3-chlorophenyl)-aniline (4fc):
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White solid; m.p.: 110–112°C; H NMR (300 MHz,
2.1k N-(4,4′,5-Trimethyl-biphenyl-2-yl)-acetamide
CDCl3): δ = 7⋅42–7⋅28 (m, 4H), 7⋅21–7⋅14 (m, 7H),
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(3ab): White solid; m.p.: 122–124°C; H NMR 6⋅55 (s, 1H, NH), 2⋅41 (s, 6H), 1⋅70 (s, 3H);
C
(300 MHz, CDCl3): δ = 7⋅95 (s, 1H, NH), 7⋅24 (t, NMR (75 MHz, CDCl3): δ = 69⋅17, 140⋅81, 139⋅76,
J = 8⋅4 Hz, 4H), 7⋅07 (s, 1H), 7⋅01 (d, J = 14⋅4 Hz, 137⋅77, 131⋅18, 130⋅19, 129⋅80, 129⋅48, 127⋅98,
1H), 2⋅40 (s, 3H), 2⋅29 (s, 3H), 2⋅24 (s, 3H), 2⋅00 (s, 127⋅60, 125⋅72, 22⋅89, 21⋅46; IR (KBr plate, CDCl3,
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3H);
C NMR (75 MHz, CDCl3): δ = 168⋅21, cm ) ν = 3241, 3027, 1657, 1526; MS (EI): m/z =
137⋅32, 136⋅50, 135⋅26, 132⋅78, 132⋅16, 131⋅03, 315, 273. Anal. Calcd. for C22H21NO: C, 83⋅78; H,
130⋅11, 129⋅57, 129⋅04, 123⋅22, 24⋅39, 21⋅11, 19⋅68, 6⋅71; N, 4⋅44. Found: C, 83⋅62; H, 6⋅86; N, 4⋅53.
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19⋅16; IR (KBr plate, CDCl3, cm ) ν = 3275, 3022,
1668, 1522; MS (EI): m/z = 253, 211. Anal. Calcd. 2.1p N-(4′-Methoxy-4,5-dimethyl-biphenyl-2-yl)-
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for C17H19NO: C, 80⋅60; H, 7⋅56; N, 5⋅53. Found: C, acetamide (3ad): White solid; m.p.: 136–138°C; H
80⋅72; H, 7⋅69; N, 5⋅59.
NMR (300 MHz, CDCl3): δ = 7⋅95 (s, 1H, NH), 7⋅27
(d, J = 8⋅7 Hz, 2H), 7⋅05–6⋅97 (m, 4H), 3⋅85 (s, 3H),
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2.1l N-(4-Chloro-4'methyl-biphenyl-2-yl)-acet-
2⋅95 (s, 3H), 2⋅24 (s, 3H), 2⋅01 (s, 3H); C NMR
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amide (3eb): White solid; H NMR (300 MHz, (75 MHz, CDCl3): δ = 168⋅16, 159⋅05, 136⋅38,
CDCl3): δ = 8⋅40 (s, 1H, NH), 7⋅29 (d, J = 8⋅40 Hz, 132⋅78, 132⋅25, 131⋅07, 130⋅44, 130⋅31, 129⋅87,
2H), 7⋅21 (d, J = 8⋅10 Hz, 3H), 7⋅12 (s, 2H), 2⋅42 (s, 123⋅21, 114⋅28, 55⋅26, 24⋅40, 19⋅66, 19⋅14; IR (KBr
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3H), 2⋅01 (s, 3H); C NMR (75 MHz, CDCl3): plate, CDCl3, cm ) ν = 3289, 1674, 1517; MS (EI):
δ = 168⋅14, 138⋅23, 135⋅81, 134⋅04, 133⋅86, 131⋅86, m/z = 269, 227. Anal. Calcd. for C17H19NO2: C,
130⋅87, 129⋅98, 128⋅98, 124⋅16, 121⋅00, 24⋅61 21⋅18; 75⋅81; H, 7⋅11; N, 5⋅20. Found: C, 75⋅94; H, 7⋅01;
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IR (KBr plate, CDCl3, cm ) ν = 3273, 2920, 1668, N, 5⋅30.
1517; MS (EI): m/z = 261, 259, 217. Anal. Calcd.
for C15H14ClNO: C, 69⋅36; H, 5⋅43; N, 5⋅39. Found: 2.1q N-(4′-Ethoxy-4,5-dimethyl-biphenyl-2-yl)-
C, 69⋅51; H, 4⋅60; N, 5⋅23.
acetamide (3ae): White solid; m.p.: 102–103°C;
H NMR (300 MHz, CDCl3): δ = 7⋅95 (s, 1H, NH),
2.1m N-(3′,4,5-Trimethyl-biphenyl-2-yl)-acetamide 7⋅25 (d, J = 8.4 Hz, 2H), 7⋅07–6⋅95 (m, 4H), 4⋅08
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(3ac): White solid; m.p.: 92–93°C; H NMR (dd, J = 6⋅9, 6⋅9 Hz, 2H), 2⋅29 (s, 3H), 2⋅24 (s, 3H),
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(300 MHz, CDCl3): δ = 7⋅98 (s, 1H, NH), 7⋅34 (t, 2⋅01 (s, 3H) 1⋅45 (t, J = 6⋅9 Hz, 3H); C NMR
J = 7⋅2 Hz, 1H), 7⋅21–7⋅09 (m, 4H), 7⋅02 (s, 1H), (75 MHz, CDCl3): δ = 168⋅16, 158⋅42, 136⋅31,
2⋅41 (s, 3H), 2⋅31 (s, 3H), 2⋅25 (s, 3H), 2⋅01 (s, 3H); 132⋅74, 132⋅24, 131⋅06, 130⋅28, 129⋅92, 123⋅18,
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C NMR (75 MHz, CDCl3): δ = 168⋅15, 138⋅64, 114⋅78, 63⋅45, 24⋅39, 19⋅66, 19⋅14, 14⋅78; IR (KBr
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138⋅22, 136⋅59, 132⋅73, 132⋅12, 130⋅95, 130⋅23, plate, CDCl3, cm ) ν = 3286, 1669, 1518; MS (EI):
129⋅95,128⋅67, 128⋅28, 126⋅10, 123⋅18, 24⋅38, m/z = 283, 241. Anal. Calcd. for C18H21NO2: C,