Page 13 of 23
The Journal of Organic Chemistry
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156.6, 127.8, 127.7, 125.7, 54.1, 35.1, 31.0, 29.4, 19.6, 13.5; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd
for C15H23N3O2Na, 300.1683; found, 300.1692.
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N'-(4-Bromobenzoyl)-N-butylnitrous hydrazide (2f)
Compound 2f was isolated in 71% yield (212 mg, yellow oil); 1H NMR (400 MHz, CDCl3) δ 9.28 (brs,
NH, 1H), 7.66 (d, J = 8.6 Hz, 2H), 7.54 (d, J = 8.5 Hz, 2H), 4.46 (t, J = 7.1 Hz, 2H), 1.88 – 1.68 (m, 2H),
1.46 – 1.29 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 164.6, 132.1, 129.6,
129.3, 129.2, 128.0, 54.1, 29.4, 19.6, 13.5; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for
C11H14BrN3O2Na, 322.0162; found, 322.0163.
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N-Butyl-N'-(4-nitrobenzoyl)nitrous hydrazide (2g)
Compound 2g was isolated in 44% yield (117 mg, yellow oil); 1H NMR (400 MHz, d6-DMSO) δ 11.33
(brs, 1H), 8.36 (d, J = 8.6 Hz, 2H), 8.08 (d, J = 8.3 Hz, 2H), 4.34 (t, J = 6.4 Hz, 2H), 1.77 – 1.65
(m, 2H), 1.42 – 1.30 (m, 2H), 0.91 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (101 MHz, d6-DMSO) δ
163.2, 150.2, 137.1, 129.8, 124.3, 53.6, 29.4, 19.5, 13.9; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd
for C11H14N4O4Na, 289.0907; found, 289.0911.
N'-Benzoyl-N-methylnitrous hydrazide (2h)
Compound 2h was isolated in 61% yield (109 mg, white solid: 115 oC-118 oC;) 1H NMR (400 MHz,
CDCl3) δ 9.27 (brs, NH, 1H), 7.82 (d, J = 7.6 Hz, 2H), 7.59 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.2 Hz,
2H), 4.16 (s, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 165.4, 133.2, 130.8, 128.9, 127.7, 41.2;
HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C8H9N3O2Na, 202.0587; found, 202.0593.
N'-Benzoyl-N-ethylnitrous hydrazide (2i)
Compound 2i was isolated in 70% yield (135 mg, yellow oil); 1H NMR (400 MHz, CDCl3) δ 9.40 (s,
1H), 7.77 (d, J = 7.5 Hz, 2H), 7.49 (t, J = 7.1 Hz, 1H), 7.35 (t, J = 7.4 Hz, 2H), 4.47 – 4.34 (m,
2H), 1.42 – 1.29 (m, 3H).13C{1H} NMR (101 MHz, CDCl3) δ 165.8, 133.0, 132.9, 130.7, 128.7,
127.8, 127.7, 49.5, 13.0. HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C9H11N3O2Na, 216.0744;
found, 216.0742.
N'-Benzoyl-N-propylnitrous hydrazide (2j)
Compound 2j was isolated in 74% yield (153 mg, yellow oil); 1H NMR (400 MHz, CDCl3) δ 9.28 (brs,
NH, 1H), 7.83 – 7.75 (m, 2H), 7.55 – 7.49 (m, 1H), 7.43 – 7.35 (m, 2H), 4.42 (t, J = 7.1 Hz, 2H),
1.90 – 1.71 (m, 2H), 0.95 (t, J = 7.4 Hz, 3H); 13C{1H} NMR (101MHz, CDCl3) δ 165.6, 133.0,
130.8, 128.8, 127.7, 56.0, 20.8, 11.0; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C10H13N3O2Na,
230.0900; found, 230.0894.
N'-Benzoyl-N-cyclopentylnitrous hydrazide (2k)
Compound 2k was isolated in 69% yield (161 mg, yellow solid:108 oC-111 oC); H NMR (400 MHz,
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CDCl3) δ 8.90 (brs, NH, 1H), 7.80 (d, J = 7.2 Hz, 2H), 7.51 (t, J = 7.4 Hz, 1H), 7.38 (t, J = 7.8 Hz,
2H), 5.19 – 5.05 (m, 1H), 2.14 – 1.96 (m, 4H), 1.85 – 1.54 (m, 4H); 13C{1H} NMR (101 MHz,
CDCl3) δ 166.2, 132.9, 130.9, 128.7, 127.8, 66.5, 30.3, 23.8; HRMS (ESI-TOF) m/z: [M + Na]+
Calcd for C12H15N3O2Na, 256.1057; found, 256.1054.
N'-Benzoyl-N-benzylnitrous hydrazide (2l)
Compound 2l was isolated in 75% yield (191 mg, white solid:113 oC-116 oC); 1H NMR (400
MHz, CDCl3) δ 9.05 (brs, NH, 1H), 7.65 (d, J = 7.7 Hz, 2H), 7.50 (t, J = 7.4 Hz, 1H), 7.39 – 7.32
(m, 2H), 7.31 (s, 5H), 5.59 (s, 2H); 13C{1H} NMR (101 MHz, CDCl3) δ 165.4, 133.5, 133.0,
130.7, 129.1, 128.9, 128.8, 128.2, 127.7, 57.6; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for
C14H13N3O2Na, 278.0900; found, 278.0909.
N-Allyl-N'-benzoylnitrous hydrazide (2m)
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