1382
W. J. Park and E. Ma
2-Tetradecanoylaminobenzoic acid (15)
(COOH); FT-IR cm−1: 1261 (COOH), 1678 (CONH), 1697
1
Yield: 96%; mp: 78-79oC; H-NMR (400 MHz, CDCl3): (COOH); GC-MS (EI) m/z: 261 [M-H2O]+.
δ
0.87 (3H, t,
CH2×10), 1.76 (2H, quint,
(2H, t, = 7.2 Hz, CH2), 7.12 (1H, dd,
H-5), 7.60 (1H, dd, = 8.0, 7.8 Hz, H-4), 8.13 (1H, d,
= 8.0 Hz, H-6), 8.77 (1H, d, = 8.8 Hz, H-3), 10.91 CH2×6), 1.68 (2H, quint,
(1H, s, NH); 13C-NMR (100 MHz, CDCl3):
14.1 (CH3), (2H, t, = 7.4 Hz, CH2), 6.95 (1H, d,
22.7 (CH2), 25.5 (CH2), 29.2 (CH2), 29.4 (CH2), 29.5 7.47 (1H, s, H-6), 8.29 (1H, d, = 8.8 Hz, H-3), 11.27
(CH2×5), 29.7 (CH2), 31.9 (CH2), 38.7 (CH2), 113.7 (C- (1H, s, NH); 13C-NMR (100 MHz, CD3OD):
13.2 (CH3),
J
= 6.2 Hz, CH3), 1.24-1.38 (20H, m,
= 14.4, 7.2 Hz, CH2), 2.46 2-Decanoylamino-5-hydroxybenzoic acid (19)
= 7.6, 7.6 Hz, Yield: 82%; mp: 157-158oC; 1H-NMR (400 MHz, CD3OD):
0.86 (3H, t, = 6.2 Hz, CH3), 1.26-1.33 (12H, m,
= 13.6, 6.8 Hz, CH2), 2.36
= 8.8 Hz, H-4),
J
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δ
J
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δ
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δ
3), 120.6 (C-5), 122.6 (C-1), 131.7 (C-6), 135.7 (C-4), 22.5 (CH2), 25.6 (CH2), 29.1 (CH2), 29.2 (CH2), 29.4
142.2 (C-2), 172.0 (CONH), 172.6 (COOH); FT-IR cm−1: (CH2×2), 31.8 (CH2), 38.0 (CH2), 117.0 (C-6), 119.2 (C-4),
1260 (COOH), 1678 (CONH), 1697 (COOH); GC-MS 120.3 (C-3), 122.0 (C-1), 133.2 (C-2), 152.9 (C-5), 170.5
(EI) m/z: 329 [M-H2O]+.
(CONH), 172.7 (COOH); FT-IR cm−1: 1262 (COOH),
1679 (CONH); GC-MS (EI) m/z: 289 [M-H2O]+.
2-Hexadecanoylaminobenzoic acid (16)
1
Yield: 94%; mp: 64-65oC; H-NMR (400 MHz, CDCl3): 2-Dodecanoylamino-5-hydroxybenzoic acid (20)
δ
0.87 (3H, t,
CH2×12), 1.76 (2H, quint,
(2H, t, = 7.4 Hz, CH2), 7.12 (1H, dd,
H-5), 7.60 (1H, dd, = 8.0, 8.0 Hz, H-4), 8.13 (1H, d,
= 8.0 Hz, H-6), 8.77 (1H, d, = 8.4 Hz, H-3), 10.92 4), 7.46 (1H, d,
(1H, s, NH); 13C-NMR (100 MHz, CDCl3): 14.1 (CH3), H-3), 11.08 (1H, s, NH); 13C-NMR (100 MHz, CD3OD):
J
= 6.4 Hz, CH3), 1.24-1.40 (24H, m, Yield: 81%; mp: 133-134oC; 1H-NMR (400 MHz, CD3OD):
= 14.4, 7.2 Hz, CH2), 2.46 0.87 (3H, t, = 6.8 Hz, CH3), 1.25-1.33 (16H, m,
= 7.6, 7.6 Hz, CH2×8), 1.69 (2H, quint, = 14.0, 7.0 Hz, CH2), 2.36
(2H, t, = 7.4 Hz, CH2), 6.97 (1H, dd, = 9.0, 2.6 Hz, H-
= 2.8 Hz, H-6), 8.30 (1H, d, = 9.2 Hz,
J
δ
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δ
δ
22.7 (CH2), 25.6 (CH2), 29.2 (CH2), 29.4 (CH2), 29.5 13.2 (CH3), 22.5 (CH2), 25.6 (CH2), 29.0 (CH2), 29.2
(CH2×7), 29.7 (CH2), 32.0 (CH2), 38.8 (CH2), 113.8 (C- (CH2), 29.3 (CH2), 29.4 (CH2), 29.5 (CH2×2), 31.9 (CH2),
3), 120.7 (C-5), 122.6 (C-1), 131.8 (C-6), 135.7 (C-4), 37.9 (CH2), 116.9 (C-6), 118.2 (C-4), 120.7 (C-3), 122.1
142.2 (C-2), 172.2 (CONH), 172.7 (COOH); FT-IR cm−1: (C-1), 133.3 (C-2), 152.9 (C-5), 169.9 (CONH), 172.8
1261 (COOH), 1679 (CONH), 1697 (COOH); GC-MS (COOH); FT-IR cm−1: 1262 (COOH), 1680 (CONH); GC-
(EI) m/z: 357 [M-H2O]+.
MS (EI) m/z: 317 [M-H2O]+.
2-Hexanoylamino-5-hydroxybenzoic acid (17)
5-Hydroxy-2-tetradecanoylaminobenzoic acid (21)
Yield: 78%; mp: 152-153oC; 1H-NMR (400 MHz, CD3OD): Yield: 81%; mp: 133-134oC; 1H-NMR (400 MHz, CD3OD):
δ
0.90 (3H, t,
1.69 (2H, quint,
= 7.6 Hz, CH2), 6.97 (1H, dd,
(1H, d, = 3.2 Hz, H-6), 8.29 (1H, d,
11.04 (1H, s, NH); 13C-NMR (100 MHz, CD3OD):
(CH3), 22.2 (CH2), 25.3 (CH2), 31.3 (CH2), 37.9 (CH2), CD3OD):
J
= 6.6 Hz, CH3), 1.33-1.36 (4H, m, CH2×2),
= 14.4, 7.2 Hz, CH2), 2.36 (2H, t,
= 9.2, 3.0 Hz, H-4), 7.46 (2H, t,
= 9.2 Hz, H-3), H-4), 7.45 (1H, d,
13.1 Hz, H-3), 11.11 (1H, s, NH); 13C-NMR (100 MHz,
13.2 (CH3), 22.5 (CH2), 25.6 (CH2), 29.0
δ
0.87 (3H, t,
CH2×10), 1.69 (2H, quint,
= 7.6 Hz, CH2), 6.96 (1H, dd,
= 2.8 Hz, H-6), 8.29 (1H, d,
J
= 6.6 Hz, CH3), 1.25-1.33 (20H, m,
= 14.0, 7.0 Hz, CH2), 2.36
= 9.2, 2.8 Hz,
= 9.2
J
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δ
δ
116.9 (C-6), 118.1 (C-4), 120.8 (C-3), 122.2 (C-1), 133.2 (CH2), 29.2 (CH2), 29.3 (CH2), 29.5 (CH2×5), 31.9
(C-2), 152.9 (C-5), 169.9 (CONH), 172.8 (COOH); FT-IR (CH2), 37.9 (CH2), 116.9 (C-6), 118.3 (C-4), 120.7 (C-3),
cm−1: 1261 (COOH), 1679 (CONH), 1697 (COOH); GC- 122.1 (C-1), 133.2 (C-2), 152.9 (C-5), 170.0 (CONH),
MS (EI) m/z: 233 [M-H2O]+.
172.8 (COOH); FT-IR cm−1: 1263 (COOH), 1681
(CONH); GC-MS (EI) m/z : 345 [M-H2O]+.
5-Hydroxy-2-octanoylaminobenzoic acid (18)
Yield: 80%; mp: 157-158oC; 1H-NMR (400 MHz, CD3OD): 2-Hexadecanoylamino-5-hydroxybenzoic acid (22)
δ
0.87 (3H, t,
1.69 (2H, quint,
= 7.6 Hz, CH2), 6.97 (1H, dd,
(1H, d, = 3.2 Hz, H-6), 8.29 (1H, d,
11.07 (1H, s, NH); 13C-NMR (100 MHz, CD3OD):
13.2 (CH3), 22.5 (CH2), 25.6 (CH2), 28.9 (CH2×2), 31.6 Hz, H-3), 11.69 (1H, s, NH); 13C-NMR (100 MHz,
(CH2), 37.9 (CH2), 116.9 (C-6), 118.6 (C-4), 120.5 (C-3), CD3OD): 14.1 (CH3), 22.7 (CH2), 25.7 (CH2), 29.3
122.1 (C-1), 133.2 (C-2), 152.8 (C-5), 170.1 (CONH), 172.8 (CH2), 29.4 (CH2), 29.5 (CH2×7), 29.7 (CH2), 31.9 (CH2),
J
= 6.8 Hz, CH3), 1.28-1.34 (8H, m, CH2×4), Yield: 77%; mp: 131-133oC; 1H-NMR (400 MHz, CD3OD):
= 14.0, 7.0 Hz, CH2), 2.36 (2H, t, 0.87 (3H, t, = 6.6 Hz, CH3), 1.26-1.33 (24H, m,
= 9.0, 3.0 Hz, H-4), 7.46 CH2×12), 1.69 (2H, quint, = 14.0, 7.0 Hz, CH2), 2.35
= 8.8 Hz, H-3), (2H, t, = 7.4 Hz, CH2), 6.89 (1H, dd, = 8.8, 2.8 Hz,
H-4), 7.46 (1H, d, = 2.8 Hz, H-6), 8.29 (1H, d, = 8.8
J
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